DFT study of cycloaddition reaction of isothiocyanates with diazoazoles to 4-imino-4H-pyrazolo{[}5,1-d] {[}1,2,3,5]thiatriazines / Subbotina Julia O.,Sadchikova Elena V.,Bakulev Vasiliy A.,Fabian Walter M. F.,Herges Rainer // INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY. - 2007. - V. 107, l. 13, SI. - P. 2479-2488.

ISSN/EISSN:

0020-7608 / нет данных

Type:

Article; Proceedings Paper

Abstract:

The mechanism of reaction of isothiocyanates with diazopyrazoles to 4-imino-4H-pyrazolo{[}5,1-d] {[}1,2,3,5]thiatriazines was investigated. It was suggested that the reaction proceeds via a pseudopericyclic cycloaddition with activation barrier of similar to 31 kcal mol(-1) (B3LYP/6-31G({*})). The mechanism was confirmed by NBO and ACID schemes. The question of regioselectivity was also explored. It was shown that an acyl substituent on the isothiocyanate led to a stabilization of the final product due to S... O interaction. (c) 2007 Wiley Periodicals, Inc.

Author keywords:

pericyclic reactions; dipolar cycloaddition; DFT; ACID; NICS; NBO THERMAL CHELETROPIC DECARBONYLATIONS; AB-INITIO; 1,3-DIPOLAR CYCLOADDITIONS; PSEUDOPERICYCLIC REACTIONS; MAGNETIC-PROPERTIES; TRANSITION-STATES; DENSITY; CYCLIZATION; REARRANGEMENT; AROMATICITY

DOI:

10.1002/qua.21351

Web of Science ID:

ISI:000249459800019

Соавторы в МНС:

—

Другие поля

Поле	Значение
Month	NOV 5
Note	10th Annual Meeting of the V-A-Fock-School on Quantum and Computational Chemistry, Kazan, RUSSIA, JUL 11-14, 2006
Organization	V A Fock Sch
Publisher	JOHN WILEY \& SONS INC
Address	111 RIVER ST, HOBOKEN, NJ 07030 USA
Language	English
Keywords-Plus	THERMAL CHELETROPIC DECARBONYLATIONS; AB-INITIO; 1,3-DIPOLAR CYCLOADDITIONS; PSEUDOPERICYCLIC REACTIONS; MAGNETIC-PROPERTIES; TRANSITION-STATES; DENSITY; CYCLIZATION; REARRANGEMENT; AROMATICITY
Research-Areas	Chemistry; Mathematics; Physics
Web-of-Science-Categories	Chemistry, Physical; Mathematics, Interdisciplinary Applications; Physics, Atomic, Molecular \& Chemical
Author-Email	julia\_subbotina@mail.ru
ResearcherID-Numbers	Subbotina, Julia/L-7131-2016
ORCID-Numbers	Subbotina, Julia/0000-0002-2227-0787
Number-of-Cited-References	56
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	7
Journal-ISO	Int. J. Quantum Chem.
Doc-Delivery-Number	210MH