Artículo
Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles
Fecha de publicación:
04/2012
Editorial:
American Chemical Society
Revista:
Journal of Organic Chemistry
ISSN:
0022-3263
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A series of 1-aryl/alkyl-1H-1,2,3,4-tetrazoles, 5-substituted 1H-tetrazoles, and 1,5- and 2,5-disubstituted 1H-tetrazoles were studied by a combination of experimental NMR (natural abundance 15N, 15N/ 1H HMBC, and 13C) and computational GIAO-NMR techniques to explore substituent effects on 15N (and 13C) NMR chemical shifts in the tetrazole (TA) moiety. Computed 15N chemical shifts via GIAO-B3LYP/6-311+G(2d,p) calculations gave satisfactory results in comparison with experimental data. Whereas N-alkylation leads to large 15N chemical shift changes, changes in the N 1-aryl derivatives bearing diverse substituent(s) are generally small except for polar ortho-substituents (COOH, NO 2). Large δδ 15N values were computed in N 1-aryl derivatives for p-COH 2 + and p-OMeH + as extreme examples of electron-withdrawing substituents on a TA moiety. © 2012 American Chemical Society.
Palabras clave:
15n Nmr
,
Tetrazoles
,
Substituent Effects
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Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Aridoss, Gopalakrishnan; Zhao, Chunqing; Borosky, Gabriela Leonor; Laali, Kenneth K.; Experimental and GIAO 15N NMR study of substituent effects in 1 H -tetrazoles; American Chemical Society; Journal of Organic Chemistry; 77; 8; 4-2012; 4152-4155
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