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Inequivalence of substitution pairs in hydroxynaphthaldehyde: A theoretical measurement by intramolecular hydrogen bond strength, aromaticity, and excited‐state intramolecular proton transfer reaction by Subrata Mahanta; Bijan Kumar Paul; Rupashree Balia Singh; Nikhil Guchhait is a Chemistry article available to read on EtoBox.

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## Abstract The inequivalence of substitution pair positions of naphthalene ring has been investigated by a theoretical measurement of hydrogen bond strength, aromaticity, and excited state intramolecular proton transfer (ESIPT) reaction as the tools in three substituted naphthalene compounds viz 1‐hydroxy‐2‐naphthaldehyde (HN12), 2‐hydroxy‐1‐naphthaldehyde (HN21), and 2‐hydroxy‐3‐naphthaldehyde (HN23). The difference in intramolecular hydrogen bond (IMHB) strength clearly reflects the inequivalence of substitution pairs where the calculated IMHB strength is found to be greater for HN12 and HN21 than HN23. The H‐bonding interactions have been explored by calculation of electron density ρ(__r__) and Laplacian ∇^2^ρ(__r__) at the bond critical point using atoms in molecule method and by calculation of interaction between σ\* of OH with lone pair of carbonyl oxygen atom using NBO analysis. The ground and excited state potential energy surfaces (PESs) for the proton transfer reaction at HF (6‐31G\*\*) and DFT (B3LYP/6‐31G\*\*) levels are similar for HN12, HN21 and different for HN23. The computed aromaticity of the two rings of naphthalene moiety at B3LYP/6‐31G\*\* method also predicts

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Author

Subrata Mahanta; Bijan Kumar Paul; Rupashree Balia Singh; Nikhil Guchhait

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0192-8651)

Published

2010

Language

EN

Field

Chemistry (Physical Sciences)