Planar 1,3 lambda(4)delta(2),2,4-benzodithiadiazine and its nonplanar 5,6,7,8-tetrafluoro derivative: Gas-phase structures studied by electron diffraction and ab initio calculations

Planar 1,3 lambda(4)delta(2),2,4-benzodithiadiazine and its nonplanar 5,6,7,8-tetrafluoro derivative: Gas-phase structures studied by electron diffraction and ab initio calculations Full article

Journal

Chemistry - A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765

Output data

Year: 2001, Volume: 7, Number: 16, Pages: 3592-3602 Pages count : 11 DOI: 10.1002/1521-3765(20010817)7:16<3592::AID-CHEM3592>3.0.CO;2-8

Tags

ab initio calculations; electron diffraction; heterocycles

Authors

Blockhuys Frank ¹ , Hinchley Sarah L. ¹ , Marakov Alexander Yu. ² , Gatilov Yuri V. ² , Zibarev Andrey V. ² , Woollins J.Derek ³ , Rankin David W.H. ¹

Affiliations

1	Department of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, United Kingdom
2	Institute of Organic Chemistry, Russian Academy of Sciences, 630 090 Novosibirsk, Russian Federation
3	(Данные Web of science) Univ St Andrews, Dept Chem, St Andrews KY16 9ST, Fife, Scotland

The gas-phase molecular structures of 1,3 lambda (4)delta (2),2,4-benzodithiadiazine and 5,6,7,8-tetrafluoro-1,3 lambda (4)delta (2),2,4-benzodithiadiazine have been investigated by ab initio calculations and electron diffraction using the SARACEN method of structural analysis. Important structural parameters (r(hl) structure) for the parent compound were found to be: < r(S=N) > 1.546(3), r(S-N) 1.697(5), r(C-S) 1.784(5), and r(C-N) 1.393(6) Angstrom. For the tetrafluoro derivative, these are (rh(1) structure): < r(S=N) > 1.552(3), r(S-N) 1.723(8), r(C-S) 1.812(9), and r(C-N) 1.396(7) Angstrom. Furthermore, the GED experiment (Gas Electron Diffraction) quite convincingly demonstrates the nonplanarity of the former and the planarity of the latter in agreement with DFT calculations; but the results contradict calculations at the MP2 level. The effect of the fluorine atoms on the conformations of the molecules is discussed.

Blockhuys F. , Hinchley S.L. , Marakov A.Y. , Gatilov Y.V. , Zibarev A.V. , Woollins J.D. , Rankin D.W.H.
Planar 1,3 lambda(4)delta(2),2,4-benzodithiadiazine and its nonplanar 5,6,7,8-tetrafluoro derivative: Gas-phase structures studied by electron diffraction and ab initio calculations
Chemistry - A European Journal. 2001. V.7. N16. P.3592-3602. DOI: 10.1002/1521-3765(20010817)7:16<3592::AID-CHEM3592>3.0.CO;2-8 WOS Scopus Scopus РИНЦ

Published print:

Aug 17, 2001

Web of science	WOS:000170714700020
Scopus	2-s2.0-0035902814 , 2-s2.0-85046910237
Elibrary	43200421
OpenAlex	W1967530638