Chemical informatics technology can be of assistance to chemists for describing reactions in numerous ways, including calculating green chemistry metrics such as process mass intensity, E-factor and atom economy. To facilitate this, chemical reactions have to be described in more precise detail than is the norm for most chemists. There are also numerous practical ways to add more green chemistry functionality to lab notebooks, such as enumerating searchable reaction transforms for environmentally favourable reactions, automatically looking up toxicity and hazard information, and others which are mentioned in the slides. This presentation was given at the Green Chemistry & Engineering conference in 2015 (Americal Chemical Society Green Chemistry Insititute).

1. Green chemistry in
chemical reactions:
informatics by design
Alex M. Clark, Ph.D.
July 2015
© 2015 Molecular Materials Informatics, Inc.
http://molmatinf.com

2. MOLECULAR MATERIALS INFORMATICS
Data Capture
• Reactions normally drawn for chemists…
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3. MOLECULAR MATERIALS INFORMATICS
Data Capture
• Reactions normally drawn for chemists…
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• … rather than computers.

4. MOLECULAR MATERIALS INFORMATICS
Necessary Content
• Many useful metrics are easy to calculate if...
• Structures for everything: must be fully
interpretable (including inorganics)
• All components classified
• Balanced stoichiometry - all atoms accounted
for whenever possible
• Multistep reactions should be handled well
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+

5. MOLECULAR MATERIALS INFORMATICS
Green Metrics
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Process Mass Intensity (PMI) =
mass of all reactants
mass of products
E-factor =
mass of waste
mass of products
Atom Economy =
Σ molecular weight products
Σ molecular weight reactants
• Trivial calculations… if the information is available.
Yield =
molar mass of product
molar mass of limiting reactant

6. MOLECULAR MATERIALS INFORMATICS
Digitally Friendly
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7. MOLECULAR MATERIALS INFORMATICS
Digitally Friendly
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primary
reactant
secondary
reactants
catalyst
solvent
intermediate
byproducts
final
product
reagent

8. MOLECULAR MATERIALS INFORMATICS
Quantities
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9. MOLECULAR MATERIALS INFORMATICS
Quantities
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10. MOLECULAR MATERIALS INFORMATICS
Green Metrics
• Totals for reactants, products & waste
• For each non-waste product: yield, PMI, E-factor,
Atom-E… always calculated, always recorded
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11. MOLECULAR MATERIALS INFORMATICS
Reaction Transforms
• Reaction = specific description of experiment
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1 2 3
4
1 2
3
4
• Transform = the generic form of a reaction

12. MOLECULAR MATERIALS INFORMATICS
Convenience
• Apply to a molecule...
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10 g

13. MOLECULAR MATERIALS INFORMATICS
Convenience
• Apply to a molecule...
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14. MOLECULAR MATERIALS INFORMATICS
Decision Making
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ProductSearchResults
Yield PMI E-factor
Atom
Economy
100% 2.18 1.18 100%
84% 12.49 11.49 93.3%
82% 19.17 18.17 87.4%
100% 8.26 7.26 56.3%
63% 8.93 7.93 73.3%

15. MOLECULAR MATERIALS INFORMATICS
Reference Information
• Green solvents: encourage
selection of least harmful
- environmental impact
- toxicity, flammability, etc.
• Looking up reactants &
reagents in a hazards
database would be useful
• Likewise for byproducts:
criteria for reaction choice
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16. MOLECULAR MATERIALS INFORMATICS
Implementation
• Primary implementation as the GREEN
LAB NOTEBOOK app (iPhone, iPad)
• Reference databases & transform
searching are works in progress
• Desktop version currently underway...
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17. MOLECULAR MATERIALS INFORMATICS
Further Work
• Applying & searching transforms, depiction
• Curation of green reaction database
• Experiment conditions: so far only scheme
and ingredients
• Improved reaction atom mapping
• Solvent applicability prediction (data bound)
• Semantic micropublications: URIs everywhere
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18. Acknowledgments
http://molmatinf.com
http://molsync.com
http://cheminf20.org
Alex M. Clark
@aclarkxyz
• ACS GCI
• Sean Ekins (Green
Solvents)
• Antony Williams
(ChemSpider)
• Inquiries to
info@molmatinf.com

19. Acknowledgments
http://molmatinf.com
http://molsync.com
http://cheminf20.org
Alex M. Clark
@aclarkxyz
• ACS GCI
• Sean Ekins (Green
Solvents)
• Antony Williams
(ChemSpider)
• Inquiries to
info@molmatinf.com