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Intramolecular charge transfer associated with hydrogen bonding effects on 2-aminobenzoic acid

Paper ID Volume ID Publish Year Pages File Format Full-Text
28698 44086 2006 14 PDF Available
Title
Intramolecular charge transfer associated with hydrogen bonding effects on 2-aminobenzoic acid
Abstract

Effect of solvents, buffer solutions of different pH and β-cyclodextrin (β-CD) on the absorption and fluorescence spectra of 2-aminobenzoic acid (2ABA) have been investigated. The inclusion complex of 2ABA with β-CD is discussed by semiempirical quantum calculations (AM1), absorption, emission, FT-IR, 1H NMR and scanning electron microscope (SEM). The Stokes shifts in 2ABA is correlated with different polarity scales suggest that 2ABA molecule is more polar in the S1 state. The increase in the excited state dipole moment values and β-CD studies confirm that the presence of intramolecular charge transfer (ICT) in 2ABA. Acidity constants for different prototropic equilibria of 2ABA in the S0 and S1 states are calculated. β-CD studies shows that (i) at pH ∼ 1, 2ABA forms 1:1 inclusion complex with β-CD, whereas at pH ∼ 7, it forms mixture of 1:1 and 1:2 inclusion complex and (ii) at pH ∼ 1, appearance of dual luminescence in higher β-CD solutions indicates carboxyl and amino groups present in the hydrophobic part of the β-CD. A mechanism is proposed to explain the inclusion process.

Keywords
2-Aminobenzoic acid; β-Cyclodextrin; Inclusion complex; Solvent and pH effects; ICT
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Intramolecular charge transfer associated with hydrogen bonding effects on 2-aminobenzoic acid
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 182, Issue 2, 31 August 2006, Pages 137–150
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us