Excited state tautomerization of 7-azaindole catalyzed by pyrazole

Karmakar, Shreetama ; Mukherjee, Moitrayee ; Chakraborty, Tapas (2013) Excited state tautomerization of 7-azaindole catalyzed by pyrazole Chemical Physics Letters, 561 . pp. 46-51. ISSN 0009-2614

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.cplett.2013.01.037

Abstract

Pyrazole, a five member cyclic azole, is reported here as an efficient catalyst for excited state tautomeric conversion of 7-azaindole. In hydrocarbon solution the two compounds efficiently form a doubly hydrogen-bonded 1:1 cyclic complex whose association constant value is found comparable with 7-azaindole dimerization constant, and according to B3LYP/6-311G++∗∗ calculation the binding energies of the complex and dimer are nearly same. In the excited state (S1), the TDDFT calculation predicts tautomer of the complex to be 13.4 kcal/mol more stable than normal form. Fluorescence spectra reveal that upon UV excitation the complex emits exclusively from the tautomeric form.

Item Type:Article
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ID Code:100289
Deposited On:07 Dec 2016 12:42
Last Modified:07 Dec 2016 12:42

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