You are not logged in.
Openly accessible

Prevalence of the thioamide {···H-N-C=S}2 synthon-solid-state (X-ray crystallography), solution (NMR) and gas-phase (theoretical) structures of O-methyl-N-aryl-thiocarbamides

Soo, Yei Ho, Bettens, Ryan P. A., Dakternieks, Dainis, Duthie, Andrew and Tiekink, Edward R.T. 2005, Prevalence of the thioamide {···H-N-C=S}2 synthon-solid-state (X-ray crystallography), solution (NMR) and gas-phase (theoretical) structures of O-methyl-N-aryl-thiocarbamides, CrystEngComm, vol. 2005, no. 7, pp. 682-689, doi: 10.1039/b514254g.

Attached Files
Name Description MIMEType Size Downloads
duthie-prevalenceof-2005.pdf Published version application/pdf 721.74KB 32

Title Prevalence of the thioamide {···H-N-C=S}2 synthon-solid-state (X-ray crystallography), solution (NMR) and gas-phase (theoretical) structures of O-methyl-N-aryl-thiocarbamides
Formatted title Prevalence of the thioamide {···H-N-C=S}2 synthon--solid-state (X-ray crystallography), solution (NMR) and gas-phase (theoretical) structures of O-methyl-N-aryl-thiocarbamides
Author(s) Soo, Yei Ho
Bettens, Ryan P. A.
Dakternieks, Dainis
Duthie, Andrew
Tiekink, Edward R.T.
Journal name CrystEngComm
Volume number 2005
Issue number 7
Start page 682
End page 689
Publisher RSC Publishing
Place of publication Cambridge, England
Publication date 2005
ISSN 1466-8033
Summary Structural investigations, i.e. solid-state (X-ray), solution (1H NMR) and gas-phase (theoretical), on molecules with the general formula MeOC(S)N(H)C6H4-4-Y: Y = H (1), NO2 (2), C(O)Me (3), Cl (4) have shown a general preference for the adoption of an E-conformation about the central C–N bond. Such a conformation allows for the formation of a dimeric hydrogen-bonded {H–N–C=S}2 synthon as the building block. In the cases of 1–3, additional C–H...O interactions give rise to the formation of tapes of varying topology. A theoretical analysis shows that the preference for the E-conformation is about the same as the crystal packing stabilisation energy and consistent with this, the compound with Y = C(O)OMe, (5), adopts a Z-conformation in the solid-state that facilitates the formation of N–H...O, C–H...O and C–H...S interactions, leading to a layer structure. Global crystal packing considerations are shown to be imperative in dictating the conformational form of molecules 1–5.
Notes First published on the web 23rd November 2005
Language eng
DOI 10.1039/b514254g
Field of Research 039904 Organometallic Chemistry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Copyright notice ©2005, The Royal Society of Chemistry
Persistent URL http://hdl.handle.net/10536/DRO/DU:30008889

Document type: Journal Article
Collections: School of Biological and Chemical Sciences
Open Access Collection
Connect to link resolver
 
Unless expressly stated otherwise, the copyright for items in DRO is owned by the author, with all rights reserved.

Every reasonable effort has been made to ensure that permission has been obtained for items included in DRO. If you believe that your rights have been infringed by this repository, please contact drosupport@deakin.edu.au.

Versions
Version Filter Type
Citation counts: TR Web of Science Citation Count  Cited 38 times in TR Web of Science
Scopus Citation Count Cited 3 times in Scopus
Google Scholar Search Google Scholar
Access Statistics: 560 Abstract Views, 32 File Downloads  -  Detailed Statistics
Created: Mon, 13 Oct 2008, 15:44:59 EST

Every reasonable effort has been made to ensure that permission has been obtained for items included in DRO. If you believe that your rights have been infringed by this repository, please contact drosupport@deakin.edu.au.