IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILES

The mechanism of the Diels-Alder reaction of 1-(2-furyl)-3-(dimethylamino)-2-propene-1-thione with various dienophiles resulting in the formation of 2H-thiopyran derivatives were discussed by evaluating global and local electrophilicity and nucleophilicity descriptors for whole series of diene and d...

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Autores principales:	SAHU,VINITA, SHARMA,PRATIBHA, KUMAR,ASHOK
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2014
Materias:	Enaminothione DFT B3LYP-6-31G* global and local reactivity descriptors
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000100019
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spelling	oai:scielo:S0717-970720140001000192015-11-12IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILESSAHU,VINITASHARMA,PRATIBHAKUMAR,ASHOK Enaminothione DFT B3LYP-6-31G* global and local reactivity descriptors The mechanism of the Diels-Alder reaction of 1-(2-furyl)-3-(dimethylamino)-2-propene-1-thione with various dienophiles resulting in the formation of 2H-thiopyran derivatives were discussed by evaluating global and local electrophilicity and nucleophilicity descriptors for whole series of diene and dienophiles at B3LYP/6-31G* level of theory. The results preluded that the polarity and charge transfer flow between diene and dienophiles was consistent with the global reactivity descriptors and substitutional pattern. The local descriptors based on Parr functions proposed by Domingo were found to be quite promising to explain the regioselectivity of cycloaddition processes. For symmetrical dienophiles viz., 2, 5, 8, 11a, 11b, 13 and 14 the local descriptors concentrates equally (50%) at both interacting sites, to allocate non-regioselective cycloadditions. However, unsymmetrical dienophiles 16,18a-e and 21 have shown a preference towards a particular regioisomer and shown high regioselectivity during cycloaddition reaction. Regional nucleophilicity at the interacting site of diene were evaluated using local nucleophilicity descriptor Nk. These outcomes were found to be in exact correlation with the experimental outcomes achieved by Bogdanowicz et al.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.59 n.1 20142014-03-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000100019en10.4067/S0717-97072014000100019
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Enaminothione DFT B3LYP-6-31G* global and local reactivity descriptors
spellingShingle	Enaminothione DFT B3LYP-6-31G* global and local reactivity descriptors SAHU,VINITA SHARMA,PRATIBHA KUMAR,ASHOK IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILES
description	The mechanism of the Diels-Alder reaction of 1-(2-furyl)-3-(dimethylamino)-2-propene-1-thione with various dienophiles resulting in the formation of 2H-thiopyran derivatives were discussed by evaluating global and local electrophilicity and nucleophilicity descriptors for whole series of diene and dienophiles at B3LYP/6-31G* level of theory. The results preluded that the polarity and charge transfer flow between diene and dienophiles was consistent with the global reactivity descriptors and substitutional pattern. The local descriptors based on Parr functions proposed by Domingo were found to be quite promising to explain the regioselectivity of cycloaddition processes. For symmetrical dienophiles viz., 2, 5, 8, 11a, 11b, 13 and 14 the local descriptors concentrates equally (50%) at both interacting sites, to allocate non-regioselective cycloadditions. However, unsymmetrical dienophiles 16,18a-e and 21 have shown a preference towards a particular regioisomer and shown high regioselectivity during cycloaddition reaction. Regional nucleophilicity at the interacting site of diene were evaluated using local nucleophilicity descriptor Nk. These outcomes were found to be in exact correlation with the experimental outcomes achieved by Bogdanowicz et al.
author	SAHU,VINITA SHARMA,PRATIBHA KUMAR,ASHOK
author_facet	SAHU,VINITA SHARMA,PRATIBHA KUMAR,ASHOK
author_sort	SAHU,VINITA
title	IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILES
title_short	IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILES
title_full	IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILES
title_fullStr	IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILES
title_full_unstemmed	IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILES
title_sort	impact of global and local reactivity descriptors on the hetero-diels-alder reaction of enaminothione with various electrophiles
publisher	Sociedad Chilena de Química
publishDate	2014
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000100019
work_keys_str_mv	AT sahuvinita impactofglobalandlocalreactivitydescriptorsontheheterodielsalderreactionofenaminothionewithvariouselectrophiles AT sharmapratibha impactofglobalandlocalreactivitydescriptorsontheheterodielsalderreactionofenaminothionewithvariouselectrophiles AT kumarashok impactofglobalandlocalreactivitydescriptorsontheheterodielsalderreactionofenaminothionewithvariouselectrophiles
_version_	1718445512907030528

IMPACT OF GLOBAL AND LOCAL REACTIVITY DESCRIPTORS ON THE HETERO-DIELS-ALDER REACTION OF ENAMINOTHIONE WITH VARIOUS ELECTROPHILES

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