Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions STRUCTURALLY AWARE APPROACH TO THE INTERPRETATION OF VIBRATIONAL SPECTRA Eugene Karpushkin, Yury Zhukov, Andrey Bogomolov

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions What makes “manual” IR interpretation challenging?  IR spectral signals are “volatile” due to overlap and influence of chemical environment  Many different factors to take into account simultaneously  Correlation tables and charts take expert’s time and efforts  Structurally aware software required!

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions ACD/Labs is a structurally aware software Drawn Structure Chemical databases Systematic naming Spectra ChromatogramsNMR spectral prediction Phys-chem property prediction

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions What does structural awareness mean?  Easy drawing of chemical structures  2D-cleaning/3D-optimization  Attaching molecule to a spectrum  Fragment structure analysis  Structure/substructure DB search  Reporting with structures  Peak-to-fragment assignment

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Spectrum Interpretation Chart Raw Spectrum Report Confirmed Structure Hit ListPeak Table Possible Fragments Hypothetic Structures Peak Analysis DB Search Compare Knowledge Base Construct Verify Assign Find Repeating More Data

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Possible Fragments Searching Database: Example 1 Raw Spectrum Report Confirmed Structure Hit ListPeak Table Hypothetic Structures Peak Analysis DB Search Compare Knowledge Base Construct Verify Assign Find Repeating More Data

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Searching Database: Example 2 Raw Spectrum Report Confirmed Structure Hit ListPeak Table Possible Fragments Hypothetic Structures Peak Analysis DB Search Compare Knowledge Base Construct Verify Assign Find Repeating More Data Candidate fragments: CH 3 – 9 hits; NO 2 – 7 hits; aromatics - 4 hits

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Peak Analysis Raw Spectrum Report Confirmed Structure Hit ListPeak Table Possible Fragments Hypothetic Structures Peak Analysis DB Search Compare Knowledge Base Construct Verify Assign Find Repeating More Data

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Knowledge Base: classes  alkanes, alkenes, alkynes, allenes, alicyclic compounds  alcohols, ethers, aldehydes, ketones, non- carbon acids, peroxy compounds, halogen compounds  carboxylic acids, halogenides, anhydrides, carbonates, carboxylates, esters  aromatic compounds, heterocycles  amides, amines, imides, imines, nitrocompounds, other N compounds  B, P, S, Se, Si compounds  inorganic ions

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Knowledge Base Knowledge Base Raw Spectrum Report Confirmed Structure Hit ListPeak Table Possible Fragments Hypothetic Structures Peak Analysis DB Search Compare Construct Verify Assign Find Repeating More Data

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions ACD/Labs Fragment Object “Atom” descriptors: * A [C,H] AnyC SatC Aryl Hal [N,O,S] Bond descriptors: Ar D Rn Ch

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Powerful means selective

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions PCA for Fragment Formulation Example set: 15 chloroanhydrides + 19 aldehydes = 34 compounds * 825 wavelengths

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions PCA for Fragment Formulation: Captured Variance

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions PCA for Fragment Formulation: Scores Plot – Structure Classes

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions PCA for Fragment Formulation: Scores Plot – Structure Classes

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions PCA for Fragment Formulation: Scores Plot – Structure Classes

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions PCA for Fragment Formulation: Bi-Plot Reveals Spectral Features 1718 cm cm cm -1

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions PCA for Fragment Formulation

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Knowledge Base is Interactive

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Structure Verification Raw Spectrum Report Confirmed Structure Hit ListPeak Table Possible Fragments Hypothetic Structures Peak Analysis DB Search Compare Knowledge Base Construct Verify Assign Find Repeating More Data

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Successful Verification is… Failed One Raw Spectrum Report Confirmed Structure Hit ListPeak Table Possible Fragments Hypothetic Structures Peak Analysis DB Search Compare Knowledge Base Construct Verify Assign Find Repeating More Data

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Assignment and Reporting Raw Spectrum Report Confirmed Structure Hit ListPeak Table Possible Fragments Hypothetic Structures Peak Analysis DB Search Compare Knowledge Base Construct Verify Assign Find Repeating More Data

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Conclusions 1. Full qualitative analysis spectral interpretation tools in the same product interface 2. Authentic Fragment Object provides almost unlimited flexibility in specifying group environment 3. Advanced tool for fragmental analysis of molecules 4. Knowledge Base with about 2400 highly selective fragments 5. Facilitated IR spectral interpretation and automated structure verification

Spectroscopy Chromatography PhysChem Naming Drawing and Databasing Enterprise Solutions Acknowledgements  Yury Zhukov  Alexey Pastutsan