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Carbamates I: Structural and conformational study of eight Methoxyphenyl-N-pyridinylcarbamates

Mocilac, Pavle and Gallagher, John F. (2012) Carbamates I: Structural and conformational study of eight Methoxyphenyl-N-pyridinylcarbamates. In: ECA Meeting, 6 Aug 2012, Bergen, Norway.

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Crystal and molecular structures of phenyl carbamates are relatively unexplored. Only 33 basic phenylcarbamates are present on the Cambridge Structure Database with no phenyl-N-pyridinylcarbamates (Scheme 1a). Our field is structural systematics and isomer grids by bridging solid state crystallography and in silico molecular modeling with conformational analysis as a central tool. A 3×3 isomer grid of nine Methoxyphenyl-N-pyridinylcarbamates (C13H12N2O3) as CxxOMe (x = para-/meta-/ortho-) was synthesized and studied to determine their crystal structures and correlate structural relationships from both ab initio calculations and the solid-state using conformational analysis. Eight of nine crystal structures were determined using single crystal X-ray diffraction. All isomers form N-H···N hydrogen bonds as the primary interaction, with one isomer (CmmOMe, Fig. 1) forming a relatively unusual disordered hydrogen bonded trimer via N-H···N interactions, while the CoxOMe isomers (Figs. 2, 3 and 5) form N-H···N hydrogen bonded dimers.

Item Type:Conference or Workshop Item (Poster)
Event Type:Conference
Additional Information:Cambridge Structural Database (CSD) information on nine Methoxyphenyl-N-pyridinylcarbamates CCDC reference codes 936019 to 936026 and 948928. Copies available,
Uncontrolled Keywords:Carbamates; Isomer grids; Conformational analysis; Structural systematics; Methoxy; Pyridine
Subjects:Physical Sciences > Chemistry
Physical Sciences > Crystallography
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-Share Alike 3.0 License. View License
Funders:PRTLI T3
ID Code:19621
Deposited On:07 Nov 2013 11:20 by John Gallagher. Last Modified 07 Nov 2013 11:20

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