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Title: Raman, IR and DFT studies of mechanism of sodium binding to urea catalyst
Authors: Kundu, Partha P.
Kumari, Gayatri
Chittoory, Arjun K.
Rajaram, Sridhar
Narayana, Chandrabhas
Keywords: Physical Chemistry
IR and Raman spectroscopy
Sulfonyl urea
Hydrogen-bonding catalyst
Conformational change
Friedel-Crafts Alkylation
Spectra-Structure Correlations
Asymmetric Catalysis
Enantioselective Reaction
Sulfonamide Derivatives
Bond Donors
Issue Date: 2015
Publisher: Elsevier Science Bv
Citation: Journal of Molecular Structure
Kundu, P. P.; Kumari, G.; Chittoory, A. K.; Rajaram, S.; Narayana, C., Raman, IR and DFT studies of mechanism of sodium binding to urea catalyst. J. Mol. Struct. 2015, 1102, 267-274.
Abstract: Bis-camphorsulfonyl urea, a newly developed hydrogen bonding catalyst, was evaluated in an enantioselective Friedel Crafts reaction. We observed that complexation of the sulfonyl urea with a sodium cation enhanced the selectivity of reactions in comparison to reactions performed with urea alone. To understand the role of sodium cation, we performed Infrared and Raman spectroscopic studies. The detailed band assignment of the molecule was made by calculating spectra using Density Functional theory. Our studies suggest that the binding of the cation takes place through the oxygen atoms of carbonyl and sulfonyl groups. Natural Bond Orbital (NBO) analysis shows the expected charge distribution after sodium binding. The changes in the geometrical parameter and charge distribution are in line with the experimentally observed spectral changes. Based on these studies, we conclude that binding of the sodium cation changes the conformation of the sulfonyl urea to bring the chiral camphor groups closer to the incipient chiral center. (C) 2015 Elsevier B.V. All rights reserved.
Description: Restricted access
ISSN: 0022-2860
Appears in Collections:Research Articles (Sridhar Rajaram)

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