NDLI: Quantum chemical investigation on the influence of amino substitution on proton affinity of oxazolidin-2-one

Content Provider	Springer Nature Link
Author	Kaur, Damanjit Sharma, Ritika
Copyright Year	2013
Abstract	The scenarios of preferred protonation sites and the absolute gas-phase proton affinities of C5- and N4-amino derivatives of oxazolidinone (OXA) molecules possessing two oxygen and two nitrogen atoms, are studied to investigate the effect of substitution of amino group on geometry, electronic structure, and proton affinities of these molecules. The natural bond orbital analysis is invoked to obtain the second-order delocalization energies, occupations of lone pairs, charge distribution, and bond orders to rationalize the obtained results. Our findings reveal a strong nucleophilicity of O1 site in C5-amino and N4-amino-substituted OXA isomers just as in un-substituted OXA. The substituent nitrogen in N4-amino-substituted OXA has comparable electrophilicity to O1 site while lesser than acyl oxygen and higher than nitrogen of OXA ring in C5-amino-substituted OXA. The PA values of C5- and N4-amino-substituted OXA isomers span in the range 172.06–205.77 kcal mol$^{−1}$ (at CBS-Q). The PA values for the potential sites increase in the range 1.96–27.08 kcal mol$^{−1}$ as a result of the amino substitution at C5 and N4 in orientation (b) while exceptionally they decrease by 0.57–2.95 kcal mol$^{−1}$ as a result of the amino substitution at N4 in orientation (a). The results for the order of PA values of potential sites have been supported by molecular electrostatic potential maps. Our findings indicate that the factors such as geometrical rearrangements, variations in atomic charge densities and electron delocalization, effect of substituent, intramolecular hydrogen bonding, and electronic changes direct the relative stabilities and proton affinities of N, C5-substituted amino OXA isomers.
Starting Page	2173
Ending Page	2191
Page Count	19
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	24
Issue Number	6
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2013-02-15
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Oxazolidinone Proton affinity Amino Substituent Relative stability Isomers NBO Conjugative interactions Anomeric interactions Molecular electrostatic potential Computer Applications in Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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