NDLI: Conformational analysis of N-isopropylbenzohydroxamic acids: crystal structure, DFT, and NMR studies

Content Provider	Springer Nature Link
Author	Przychodzeń, Witold Chojnacki, Jarosław
Copyright Year	2008
Abstract	X-ray crystal structure determinations together with density functional theory (DFT) calculations in vacuo and NMR studies in solution have been carried out for 4-MeOC$_{6}$H$_{4}$CONPr$^{i}$OH 2a and 3,5-(NO$_{2}$)$_{2}$C$_{6}$H$_{3}$CONPr$^{i}$OH 2b. The results were compared with that for the respective N-methyl benzohydroxamic acids. For crystal structures as well as for DFT-optimized geometries of 2 (both isomers) in vacuo, the effect of substituents in aromatic ring manifested by changing of charges is inconspicuous. Studies of potential energy surfaces showed that libration barrier around ω $_{1}$ = 0° is low enough to make electron conjugation feasible, and that for 2b rotation barrier around C(O)N bond is higher by 6 kcal/mol and additionally, that rotation around N–C bond is hindered. A careful analysis of low-temperature $^{1}$H NMR spectra confirmed the greater stability of Z-2a, the greater rigidity of E-2b and the influence of solvent on both isomers population. Despite solvent-dependent conformational alteration, both 2a and 2b crystallize exclusively as E isomers from ethyl acetate solution. Correlations of absolute $^{1}$H, $^{13}$C, and $^{15}$N shielding calculations with experimental data were also analyzed.
Starting Page	637
Ending Page	644
Page Count	8
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	19
Issue Number	4
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2008-06-26
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Hydroxamic acids X-ray structure DFT calculations Substituent effects Conformations Absolute nuclear shieldings Theoretical and Computational Chemistry Physical Chemistry Computer Applications in Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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