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H-1 NMR Chemical Shifts of Cyclopropane and Cyclobutane: A Theoretical Study

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2013
Authors
Baranac-Stojanović, Marija
Stojanović, Milovan
Article (Published version)
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Abstract
This study was undertaken in order to rationalize the peculiar H-1 NMR chemical shifts of cyclopropane (delta 0.22) and cyclobutane (delta 1.98) which are shifted upfield and downfield with respect to larger cycloalkanes (delta 1.44-1.54). This is conventionally accounted for by shielding contributions arising from an aromatic-like ring current in cyclopropane, involving six electrons in the three C-C bonds, and deshielding coming from the sigma antiaromatic CC framework of cyclobutane. The shielding pattern arising from the cyclopropane and cyclobutane CC framework response to a perpendicular magnetic field was visualized as two-dimensional grid distribution of NICS values. Further insight into the origin of chemical shift values was obtained by the NCS-NBO analysis of proton shielding tensor. In the case of cyclopropane, the CC framework shielding pattern implies the existence of both delocalized and localized currents that have a dominant shielding effect on protons. The magnitude o...f C-H bonds shielding effect is significant, too. Unlike the conventional interpretation, the CC framework shields cyclobutane hydrogens, and its response to a perpendicular magnetic field is quite similar to responses of other planar sigma CC frameworks.

Source:
Journal of Organic Chemistry, 2013, 78, 4, 1504-1507
Publisher:
  • Amer Chemical Soc, Washington
Projects:
  • Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)

DOI: 10.1021/jo3025863

ISSN: 0022-3263

PubMed: 23330566

WoS: 000315254100019

Scopus: 2-s2.0-84873955750
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1284
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