Video of this presentation can be found here: http://www.youtube.com/watch?v=-rNGkmNTdLc. This talk was given as an oral presentation at the ACS 244th National Meeting held in Philadelphia, PA on August 20, 2012. This talk examined the advantages of being an undergraduate student in a research group using Open Notebook Science. Additionally, this talk examined how to use solubility tools to choose a recrystallization solvent and to plan a reaction synthesis.
A 10-15 minute presentation on my research conducted in the chemistry department of Drexel University for students interested in participating in undergraduate research.
Drexel College of Arts and Sciences (COAS) Research Day 2013mcbridemj
A presentation of my research involving using organic solubility predictions to optimize the process of choosing a recrystallization solvent. This research was conducted using Open Notebook Science to promote the sharing and access of the results and findings. This presentation was given as a 10 minute oral presentation for the 2013 COAS research day at Drexel University on April 9, 2013.
INTRODUCTION
COMPARISION BETWEEN FIXED BED VS FLUIDISED BED REACTOR
SELECTION CRITERIA FOR CATALYST REACTOR
DESIGN OF CATALYST REACTOR
DESIGN OF DEACTIVATION OF CATALYST
DETERMINATION OF THE EQUILIBRIUM CONSTANT FOR THE FORMATION OF TRI-IODIDE IONAugustine Adu
A LABORATORY WORK THAT WILL HELP ANYONE TO DETERMINE EQUILIBRIUM CONSTANT OF TRI-IODIDE ION.
THE EQUILIBRIUM CONSTANT IS NOT DIRECTLY DETERMINED, THIS PIECE WILL GIVE A WAY TO HOW IT IS DONE.
Measuring pKas, logP and Solubility by Automated titrationJon Mole
Presentation by Sirius Analytical covering measurement of pKa, LogP, LogD, Solubility, Supersaturation and precipitation kinetics.
For more details visit www.sirius-analytical.com
A 10-15 minute presentation on my research conducted in the chemistry department of Drexel University for students interested in participating in undergraduate research.
Drexel College of Arts and Sciences (COAS) Research Day 2013mcbridemj
A presentation of my research involving using organic solubility predictions to optimize the process of choosing a recrystallization solvent. This research was conducted using Open Notebook Science to promote the sharing and access of the results and findings. This presentation was given as a 10 minute oral presentation for the 2013 COAS research day at Drexel University on April 9, 2013.
INTRODUCTION
COMPARISION BETWEEN FIXED BED VS FLUIDISED BED REACTOR
SELECTION CRITERIA FOR CATALYST REACTOR
DESIGN OF CATALYST REACTOR
DESIGN OF DEACTIVATION OF CATALYST
DETERMINATION OF THE EQUILIBRIUM CONSTANT FOR THE FORMATION OF TRI-IODIDE IONAugustine Adu
A LABORATORY WORK THAT WILL HELP ANYONE TO DETERMINE EQUILIBRIUM CONSTANT OF TRI-IODIDE ION.
THE EQUILIBRIUM CONSTANT IS NOT DIRECTLY DETERMINED, THIS PIECE WILL GIVE A WAY TO HOW IT IS DONE.
Measuring pKas, logP and Solubility by Automated titrationJon Mole
Presentation by Sirius Analytical covering measurement of pKa, LogP, LogD, Solubility, Supersaturation and precipitation kinetics.
For more details visit www.sirius-analytical.com
The movement of molecules from one phase to another is called partitioning.
If two immiscible phases are placed adjacent to each other, the solute will distribute itself between two immiscible phases until equilibrium is attained; therefore no further transfer of solute occurs.
Standardization of Acids and bases.
2. Determination of pKa and pKb values
3. Preparation of solutions of different pH & buffer capacities.
4. Determination of phase diagram of binary systems.
Determination of distribution coefficients.
6. Determination of molecular weight by Victor Meyer’s Method.
7. Determination of heats of solutions by measuring solubility as a function of temperature
(Van’t Hoff equation.)
Solutions: types and properties of solutions. Units of concentration, ideal and real
solutions. Henry’s law, distribution of solids between two immiscible liquids, distribution
law. Partition coefficient and solvent extraction.
Jean-Claude Bradley presents at the University of Delaware Tuesday Tech Talks on February 12, 2013. The aim is to make a compelling case that openness is valuable to the educational process and augmenting scientific knowledge. Specific examples in chemistry relating to solubility, melting point and recrystallization will be detailed, as well as the technical solutions that have proved most useful.
Jean-Claude Bradley presents at the American Chemical Society meeting on August 20, 2012. Examples are first presented to demonstrate how access to Open Notebooks can provide critical information not usually shared in the traditional publication process. The use of Google App Scripts to look up chemical properties allows for the use of Google Spreadsheets as a self-contained dashboard to plan and analyze chemical reactions. The concept of the Open Chemical Property Matrix (OCPM) is introduced and a smartphone app to suggest recrystallization solvents is then presented.
The movement of molecules from one phase to another is called partitioning.
If two immiscible phases are placed adjacent to each other, the solute will distribute itself between two immiscible phases until equilibrium is attained; therefore no further transfer of solute occurs.
Standardization of Acids and bases.
2. Determination of pKa and pKb values
3. Preparation of solutions of different pH & buffer capacities.
4. Determination of phase diagram of binary systems.
Determination of distribution coefficients.
6. Determination of molecular weight by Victor Meyer’s Method.
7. Determination of heats of solutions by measuring solubility as a function of temperature
(Van’t Hoff equation.)
Solutions: types and properties of solutions. Units of concentration, ideal and real
solutions. Henry’s law, distribution of solids between two immiscible liquids, distribution
law. Partition coefficient and solvent extraction.
Jean-Claude Bradley presents at the University of Delaware Tuesday Tech Talks on February 12, 2013. The aim is to make a compelling case that openness is valuable to the educational process and augmenting scientific knowledge. Specific examples in chemistry relating to solubility, melting point and recrystallization will be detailed, as well as the technical solutions that have proved most useful.
Jean-Claude Bradley presents at the American Chemical Society meeting on August 20, 2012. Examples are first presented to demonstrate how access to Open Notebooks can provide critical information not usually shared in the traditional publication process. The use of Google App Scripts to look up chemical properties allows for the use of Google Spreadsheets as a self-contained dashboard to plan and analyze chemical reactions. The concept of the Open Chemical Property Matrix (OCPM) is introduced and a smartphone app to suggest recrystallization solvents is then presented.
Jean-Claude Bradley presents on Open Notebook Science: Transparency in Research on October 23, 2012 at Georgia Tech for Open Access Week. Topics include solubility, melting points, a recrystallization app, the Chemical Information Retrieval class at Drexel University and the Open Chemical Property Matrix (OCPM). YouTube recording here: http://youtu.be/XpRyfdNuMrQ
Development of Dynamic Models for a Reactive Packed Distillation ColumnCSCJournals
This work has been carried out to develop dynamic models for a reactive packed distillation column using the production of ethyl acetate as the case study. The experimental setup for the production of ethyl acetate was a pilot scale packed column divided into condenser, rectification, acetic acid feed, reaction, ethanol feed, stripping and reboiler sections. The reaction section was filled with Amberlyst 15 catalyst while the rectification and the stripping sections were both filled raschig rings. The theoretical models for each of the sections of the column were developed from first principles and solved with the aid of MATLAB R2011a. Comparisons were made between the experimental and theoretical results by calculating the percentage residuals for the top and bottom segment temperatures of the column. The results obtained showed that there were good agreements between the experimental and theoretical top and bottom segment temperatures because the calculated percentage residuals were small. Therefore, the developed dynamic models can be used to represent the reactive packed distillation column.
Optimization of ZLD in Distillery Industry by Reverse Osmosis Process for Pre...ijceronline
In this study, the effects of Operating Pressure, Potential Hydrogen, Oxidation Reduction Potential and Anti Scaling Agent on multi responses like Permeate, COD, Total Solids, Conductivity and Hardness in the Reverse Osmosis Process were experimentally investigated on RO 8100 ST8 PT44 400Wl machine. The settings of RO parameters were determined by using Taguchi’s experimental design method. Orthogonal arrays of Taguchi, the signal-to-noise (S/N) ratio, the analysis of variance (ANOVA) are employed to find the optimal levels and to analyze the effect of the RO parameters. Results show that potential of hydrogen, operating pressure, oxidation reduction potential and anti scaling agent are the four Parameters that influence the Permit more effectively and COD, Total Solids, Conductivity and Hardness respectively. Finally, the ranges for best RO conditions are proposed for ZLD process.
Jean-Claude Bradley (Drexel University), Matthew McBride (Drexel University) and Andrew Lang (Oral Roberts University) presented at the White House Open Science Poster Session on June 20, 2013. Open Notebook Science examples of melting point, solubility and recrystallization Open Data and Open Modeling were presented.
A talk I gave on August 19, 2012 at the 2012 ACS 244th national meeting held in Philadelphia, PA. This talk was given as a part of a series of 8 minutes long "lightening talks" on a variety of topics in chemistry and cheminfomatics. This talk looked at errors and missing information from literature in the field of chemistry.
In his public lecture, Christian Timmerer provides insights into the fascinating history of video streaming, starting from its humble beginnings before YouTube to the groundbreaking technologies that now dominate platforms like Netflix and ORF ON. Timmerer also presents provocative contributions of his own that have significantly influenced the industry. He concludes by looking at future challenges and invites the audience to join in a discussion.
The Art of the Pitch: WordPress Relationships and SalesLaura Byrne
Clients don’t know what they don’t know. What web solutions are right for them? How does WordPress come into the picture? How do you make sure you understand scope and timeline? What do you do if sometime changes?
All these questions and more will be explored as we talk about matching clients’ needs with what your agency offers without pulling teeth or pulling your hair out. Practical tips, and strategies for successful relationship building that leads to closing the deal.
UiPath Test Automation using UiPath Test Suite series, part 4DianaGray10
Welcome to UiPath Test Automation using UiPath Test Suite series part 4. In this session, we will cover Test Manager overview along with SAP heatmap.
The UiPath Test Manager overview with SAP heatmap webinar offers a concise yet comprehensive exploration of the role of a Test Manager within SAP environments, coupled with the utilization of heatmaps for effective testing strategies.
Participants will gain insights into the responsibilities, challenges, and best practices associated with test management in SAP projects. Additionally, the webinar delves into the significance of heatmaps as a visual aid for identifying testing priorities, areas of risk, and resource allocation within SAP landscapes. Through this session, attendees can expect to enhance their understanding of test management principles while learning practical approaches to optimize testing processes in SAP environments using heatmap visualization techniques
What will you get from this session?
1. Insights into SAP testing best practices
2. Heatmap utilization for testing
3. Optimization of testing processes
4. Demo
Topics covered:
Execution from the test manager
Orchestrator execution result
Defect reporting
SAP heatmap example with demo
Speaker:
Deepak Rai, Automation Practice Lead, Boundaryless Group and UiPath MVP
zkStudyClub - Reef: Fast Succinct Non-Interactive Zero-Knowledge Regex ProofsAlex Pruden
This paper presents Reef, a system for generating publicly verifiable succinct non-interactive zero-knowledge proofs that a committed document matches or does not match a regular expression. We describe applications such as proving the strength of passwords, the provenance of email despite redactions, the validity of oblivious DNS queries, and the existence of mutations in DNA. Reef supports the Perl Compatible Regular Expression syntax, including wildcards, alternation, ranges, capture groups, Kleene star, negations, and lookarounds. Reef introduces a new type of automata, Skipping Alternating Finite Automata (SAFA), that skips irrelevant parts of a document when producing proofs without undermining soundness, and instantiates SAFA with a lookup argument. Our experimental evaluation confirms that Reef can generate proofs for documents with 32M characters; the proofs are small and cheap to verify (under a second).
Paper: https://eprint.iacr.org/2023/1886
Epistemic Interaction - tuning interfaces to provide information for AI supportAlan Dix
Paper presented at SYNERGY workshop at AVI 2024, Genoa, Italy. 3rd June 2024
https://alandix.com/academic/papers/synergy2024-epistemic/
As machine learning integrates deeper into human-computer interactions, the concept of epistemic interaction emerges, aiming to refine these interactions to enhance system adaptability. This approach encourages minor, intentional adjustments in user behaviour to enrich the data available for system learning. This paper introduces epistemic interaction within the context of human-system communication, illustrating how deliberate interaction design can improve system understanding and adaptation. Through concrete examples, we demonstrate the potential of epistemic interaction to significantly advance human-computer interaction by leveraging intuitive human communication strategies to inform system design and functionality, offering a novel pathway for enriching user-system engagements.
GDG Cloud Southlake #33: Boule & Rebala: Effective AppSec in SDLC using Deplo...James Anderson
Effective Application Security in Software Delivery lifecycle using Deployment Firewall and DBOM
The modern software delivery process (or the CI/CD process) includes many tools, distributed teams, open-source code, and cloud platforms. Constant focus on speed to release software to market, along with the traditional slow and manual security checks has caused gaps in continuous security as an important piece in the software supply chain. Today organizations feel more susceptible to external and internal cyber threats due to the vast attack surface in their applications supply chain and the lack of end-to-end governance and risk management.
The software team must secure its software delivery process to avoid vulnerability and security breaches. This needs to be achieved with existing tool chains and without extensive rework of the delivery processes. This talk will present strategies and techniques for providing visibility into the true risk of the existing vulnerabilities, preventing the introduction of security issues in the software, resolving vulnerabilities in production environments quickly, and capturing the deployment bill of materials (DBOM).
Speakers:
Bob Boule
Robert Boule is a technology enthusiast with PASSION for technology and making things work along with a knack for helping others understand how things work. He comes with around 20 years of solution engineering experience in application security, software continuous delivery, and SaaS platforms. He is known for his dynamic presentations in CI/CD and application security integrated in software delivery lifecycle.
Gopinath Rebala
Gopinath Rebala is the CTO of OpsMx, where he has overall responsibility for the machine learning and data processing architectures for Secure Software Delivery. Gopi also has a strong connection with our customers, leading design and architecture for strategic implementations. Gopi is a frequent speaker and well-known leader in continuous delivery and integrating security into software delivery.
DevOps and Testing slides at DASA ConnectKari Kakkonen
My and Rik Marselis slides at 30.5.2024 DASA Connect conference. We discuss about what is testing, then what is agile testing and finally what is Testing in DevOps. Finally we had lovely workshop with the participants trying to find out different ways to think about quality and testing in different parts of the DevOps infinity loop.
Elevating Tactical DDD Patterns Through Object CalisthenicsDorra BARTAGUIZ
After immersing yourself in the blue book and its red counterpart, attending DDD-focused conferences, and applying tactical patterns, you're left with a crucial question: How do I ensure my design is effective? Tactical patterns within Domain-Driven Design (DDD) serve as guiding principles for creating clear and manageable domain models. However, achieving success with these patterns requires additional guidance. Interestingly, we've observed that a set of constraints initially designed for training purposes remarkably aligns with effective pattern implementation, offering a more ‘mechanical’ approach. Let's explore together how Object Calisthenics can elevate the design of your tactical DDD patterns, offering concrete help for those venturing into DDD for the first time!
GraphRAG is All You need? LLM & Knowledge GraphGuy Korland
Guy Korland, CEO and Co-founder of FalkorDB, will review two articles on the integration of language models with knowledge graphs.
1. Unifying Large Language Models and Knowledge Graphs: A Roadmap.
https://arxiv.org/abs/2306.08302
2. Microsoft Research's GraphRAG paper and a review paper on various uses of knowledge graphs:
https://www.microsoft.com/en-us/research/blog/graphrag-unlocking-llm-discovery-on-narrative-private-data/
Why You Should Replace Windows 11 with Nitrux Linux 3.5.0 for enhanced perfor...SOFTTECHHUB
The choice of an operating system plays a pivotal role in shaping our computing experience. For decades, Microsoft's Windows has dominated the market, offering a familiar and widely adopted platform for personal and professional use. However, as technological advancements continue to push the boundaries of innovation, alternative operating systems have emerged, challenging the status quo and offering users a fresh perspective on computing.
One such alternative that has garnered significant attention and acclaim is Nitrux Linux 3.5.0, a sleek, powerful, and user-friendly Linux distribution that promises to redefine the way we interact with our devices. With its focus on performance, security, and customization, Nitrux Linux presents a compelling case for those seeking to break free from the constraints of proprietary software and embrace the freedom and flexibility of open-source computing.
Essentials of Automations: The Art of Triggers and Actions in FMESafe Software
In this second installment of our Essentials of Automations webinar series, we’ll explore the landscape of triggers and actions, guiding you through the nuances of authoring and adapting workspaces for seamless automations. Gain an understanding of the full spectrum of triggers and actions available in FME, empowering you to enhance your workspaces for efficient automation.
We’ll kick things off by showcasing the most commonly used event-based triggers, introducing you to various automation workflows like manual triggers, schedules, directory watchers, and more. Plus, see how these elements play out in real scenarios.
Whether you’re tweaking your current setup or building from the ground up, this session will arm you with the tools and insights needed to transform your FME usage into a powerhouse of productivity. Join us to discover effective strategies that simplify complex processes, enhancing your productivity and transforming your data management practices with FME. Let’s turn complexity into clarity and make your workspaces work wonders!
Removing Uninteresting Bytes in Software FuzzingAftab Hussain
Imagine a world where software fuzzing, the process of mutating bytes in test seeds to uncover hidden and erroneous program behaviors, becomes faster and more effective. A lot depends on the initial seeds, which can significantly dictate the trajectory of a fuzzing campaign, particularly in terms of how long it takes to uncover interesting behaviour in your code. We introduce DIAR, a technique designed to speedup fuzzing campaigns by pinpointing and eliminating those uninteresting bytes in the seeds. Picture this: instead of wasting valuable resources on meaningless mutations in large, bloated seeds, DIAR removes the unnecessary bytes, streamlining the entire process.
In this work, we equipped AFL, a popular fuzzer, with DIAR and examined two critical Linux libraries -- Libxml's xmllint, a tool for parsing xml documents, and Binutil's readelf, an essential debugging and security analysis command-line tool used to display detailed information about ELF (Executable and Linkable Format). Our preliminary results show that AFL+DIAR does not only discover new paths more quickly but also achieves higher coverage overall. This work thus showcases how starting with lean and optimized seeds can lead to faster, more comprehensive fuzzing campaigns -- and DIAR helps you find such seeds.
- These are slides of the talk given at IEEE International Conference on Software Testing Verification and Validation Workshop, ICSTW 2022.
Dev Dives: Train smarter, not harder – active learning and UiPath LLMs for do...UiPathCommunity
💥 Speed, accuracy, and scaling – discover the superpowers of GenAI in action with UiPath Document Understanding and Communications Mining™:
See how to accelerate model training and optimize model performance with active learning
Learn about the latest enhancements to out-of-the-box document processing – with little to no training required
Get an exclusive demo of the new family of UiPath LLMs – GenAI models specialized for processing different types of documents and messages
This is a hands-on session specifically designed for automation developers and AI enthusiasts seeking to enhance their knowledge in leveraging the latest intelligent document processing capabilities offered by UiPath.
Speakers:
👨🏫 Andras Palfi, Senior Product Manager, UiPath
👩🏫 Lenka Dulovicova, Product Program Manager, UiPath
A tale of scale & speed: How the US Navy is enabling software delivery from l...sonjaschweigert1
Rapid and secure feature delivery is a goal across every application team and every branch of the DoD. The Navy’s DevSecOps platform, Party Barge, has achieved:
- Reduction in onboarding time from 5 weeks to 1 day
- Improved developer experience and productivity through actionable findings and reduction of false positives
- Maintenance of superior security standards and inherent policy enforcement with Authorization to Operate (ATO)
Development teams can ship efficiently and ensure applications are cyber ready for Navy Authorizing Officials (AOs). In this webinar, Sigma Defense and Anchore will give attendees a look behind the scenes and demo secure pipeline automation and security artifacts that speed up application ATO and time to production.
We will cover:
- How to remove silos in DevSecOps
- How to build efficient development pipeline roles and component templates
- How to deliver security artifacts that matter for ATO’s (SBOMs, vulnerability reports, and policy evidence)
- How to streamline operations with automated policy checks on container images
Elizabeth Buie - Older adults: Are we really designing for our future selves?
Open Notebook Science talk at the 2012 ACS
1. Leveraging Open Notebook
Science for solubility and
melting point predictions for
optimizing reactions and
recrystallizations
CINF
ACS Symposia #244
Philadelphia, PA
Matthew McBride
Undergraduate Chemistry Major
Drexel University
Bradley Research Group
August 20, 2012
2. Advantages of ONS for
Undergraduate Research
Gain organization skills and learn how
to properly present experiments
Receive timely feedback and corrective
input
Documentation of a student’s
contribution to a project
3. Organization and Presentation
Updating the log the day the experiment is performed
requires a student to keep an organized record of the
lab work
(http://onschallenge.wikispaces.com/EXP324)
Eliminates long term reliance on handwritten notes
and allows the log to be recorded when the
experiment is still fresh in the student’s memory
5. Correction and Input
Using ONS allows the student to receive needed
advice and guidance from the mentor directly on the
experiment’s page
(http://onschallenge.wikispaces.com/EXP255)
(http://onschallenge.wikispaces.com/EXP229)
Allows the student to understand where an error was
made and how to avoid repeating the mistake
6. Documentation
Allows a student’s work and contribution to a project
to be documented
(http://onschallenge.wikispaces.com/list+of+experiments)
Provides graduate schools with the ability to view
exactly what research an applicant has conducted
7. Solubility
Important when choosing a
recrystallization solvent
Accurate solubility predictions for a
compound allows the optimal solvent to
be used
8. Preferred Solvent
Characteristics
Does not react with the compound
being recrystallized
High solubility at boiling point, but low
solubility at room temperature
A boiling point that allows for easy
drying of the product
Miscibility with water
9. Predicting Solubility with
Abraham Descriptors
Five descriptors for each solute and each solvent
The descriptors for over 80 solvents, including some
ethanol/water mixtures, are known
Descriptors for a solute can be experimentally
determined by measuring the solubility in 5 solvents
Descriptors for a solute can be predicted using AD
Model003
Using the solute descriptors, the solubility in any of
the solvents with known descriptors can be predicted
(http://onschallenge.wikispaces.com/Benzoic+acid+-+Abraham) [William Acree]
10. Solubility Predictions
Using ONS Webservices, can list the predicted
solubility for a compound
Trans-dibenzalacetone
(www.chemspider.com/55
5548)
Solvent Model003 AD Measured Experimental BP
(M) (M) (M) (°C)
(http://showme.physics.drexel.edu/onsc/models/solventselector.php?csids=555548)
[Andrew Lang]
11. Solubility Curves
Using a melting point, temperature dependent
solubility curves are generated
Assumes that at the melting point the compound is
miscible with the solvent
Solubility in Ethanol (Concentration M vs. Temperature °C)
[Andrew Lang] (http://showme.physics.drexel.edu/onsc/models/solventselector.php?csids=555548)
12. Measuring Solubility
Surprisingly difficult. Must be sure the solution is at
saturation, while avoiding supersaturated solutions
(http://usefulchem.blogspot.com/2010/07/general-transparent-solubility.html)
13. Temperature Controlled Shake
Flask Method
Add solute to the vials with the solvent and allow to
shake in the 25°C water bath
(http://onschallenge.wikispaces.com/e
xp324)
14. Temperature Controlled Shake
Flask Method
Measure the solubility using HNMR
Need to take two consecutive measurements without
the solubility changing to confirm the solution is
saturated
(http://onschallenge.wikispaces.com/EXP311)
15. Measuring Solubility with NMR
Compare integration of solute and solvent peaks in
saturated solutions using google app scripts
1.5M Saturated solution of dibenzalacetone in THF
THF
Dibenzalacetone
(http://onschallenge.wikispaces.com/EXP308)
[Andrew Lang]
16. Benefits of Solubility
Curves
These temperature dependent solubility
curves allow a solvent with the greatest
difference between solubility at room
temperature and at the boiling point to
be used
Reduces reliance on only recrystallizing
in solvents listed in literature
Optimizes the process of choosing a
recrystallization solvent
[Andrew Lang]
17. Example
The solvents used to recrystallize compounds in
organic teaching labs can be improved
Trans-dibenzalacetone
(http://showme.physics.drexel.edu/onsc/reactionattempts/advancedsearch.php?compound=&solvent=&reactiontype
=&researcher=Matthew+McBride)
Aldol condensation between two molecules of
benzaldehyde and one molecule of acetone
[Andrew Lang]
19. Organic Teaching Labs
Many recrystallize in ethyl acetate
(http://classes.kvcc.edu/chm230/MIXED%20ALDOL%20CONDENSATION.pdf)
(http://www.xula.edu/chemistry/documents/orgleclab/Aldol_notes.pdf)
Is there a different solvent that could be used?
20. SmartPhone App
This app predicts the recrystallization yields of any
compound in different solvents using the solubility
curves:
(http://onschallenge.wikispaces.com/recrystallization)
Provides experimental and predicted values for
melting point and LogP
[Andrew Lang]
21. SmartPhone App
Enter compound identification (SMILES, CSID,
name…etc), and desired parameters
(http://onschallenge.wikispaces.com/rec
ation)
[Andrew Lang]
22. SmartPhone App
Lists solvents and their predicted recrystallization
yield
(http://onschallenge.wikispaces.com/recrystalliz
ation)
Prediction is generated by the temperature
[Andrew Lang]
23. Comparison
Ethyl acetate (predicted yield of 69%) vs ethanol
(predicted yield of 91%)
Ethyl acetate 2.06M
0.62M
Ethanol
1.1M
0.09M
(http://showme.physics.drexel.edu/onsc/m
odels/solventselector.php?csids=555548)
[Andrew Lang]
24. Solubility at Boiling
Cannot be too low or an impractical
recrystallization solvent
Example: Dibenzalacetone in hexane
(predicted yield of 90%)
25. Hexane
0.3M
(http://showme.physics.drexel.edu/onsc/models/solventselector.php?csids=555548)
[Andrew Lang]
Too insoluble at the boiling point
To recrystallize 1 gram of product (4 mmol), would
need approximately 13 mL of hexane
26. Designing reactions using
solubility
These solubility tools can be used to
choose a solvent for a reaction
Finding a solvent in which the reactants
are soluble, but the product is insoluble.
This allows the product to be recovered
by a simple filtration
27. Example
Derivatives of dibenzalacetone may be synthesized
by altering the aldehyde used
From a library of derivatives, the following compound
was the top hit for the docking site of Taxol
(http://usefulchem.wikispaces.com/D-EXP022)
(http://www.chemspider.com/28190813)
Uses phenanthrene-9-carboxaldehyde [Andrew Lang]
29. Synthesis Planning
Desire a solvent that the aldehyde is soluble
in, but the product is not
The product was predicted as having very low
solubility (<0.000M) in all solvents
NaOH used as the catalyst, so needs to be
soluble in the solvent
(http://showme.physics.drexel.edu/onsc/models/solventselector.php?csids=281908
13) [Andrew Lang]
30. Synthesis Planning
NaOH is soluble in methanol, so check aldehyde
solubility
Phenanthrene-9-carboxaldehyde
(http://www.chemspider.com/708
06)
Model003 AD Measured Experimental BP
Solvent (M) (M) (M) (°C)
(http://showme.physics.drexel.edu/onsc/models/solventselector.php?csids=70806)
[Andrew Lang]
31. Synthesis Planning
Conclusion: Using methanol as the
reaction solvent should allow the
aldehyde be dissolved into solution, but
will cause the product to precipitate
32. Synthesis
Created an approximately 0.016M
solution of phenanthrene-9-
carboxaldehyde in methanol
Added acetone and then a large excess
of NaOH (catalyst) to the reaction
mixture
Stirred mixture without heat over two
days
(http://usefulchem.wikispaces.com/EXP286)
35. Recrystallization
Used benzene
(http://usefulchem.wikispaces.com/EXP286)
Melting Point: 264-265°
36. HNMR
Spectrum of product (http://www.ch
emspider.com/
28190813)
Benzene peak in
CDCl3
16Hz Trans Coupling
(http://usefulchem.wikispaces.com/EXP286) [Andrew Lang]
37. Summary
Open Notebook Science provides
advantages to an undergraduate
researcher
Measured and predicted solubilities can
be used to optimize recrystallizations
Predicted solubilities can be used to
plan the synthesis and optimize the
recovery of the product
http://lxsrv7.oru.edu/~alang/solubility/soltemp.php?csids=555548&cs=0.092&solvent=ethanol&solmp=-114.1&solbp=78.2&limreact=0.3&limprod=0.03http://onschallenge.wikispaces.com/AbrahamDescriptorsModel003Don’t use an ethanol/water mixture, use another solvent Assumption of model: At melting point, solute is micible with solvent
Mention NMR method
Link to recrystallization page and webservices
http://lxsrv7.oru.edu/~alang/solubility/soltemp.php?csids=555548&cs=.624&solvent=ethyl%20acetate&solmp=-83.6&solbp=73.9&limreact=0.3&limprod=0.03State from bp to rtWrite sol at 25C and sol at bp
http://usefulchem.wikispaces.com/D-EXP022From a library of derivatives, it was the hop hit for the docking site of taxol