Conformational studies by dynamic NMR. 50. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution
Publication type: Journal Article
Publication date: 1993-10-01
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Barriers for the E,Z interconversion of atropisomers of 1-naphthyl sulfoxides (ArSOR) having a methyl group at position 2 of the naphthalene moiety were measured by variable-temperature NMR. Their values were found to cover the range 10.6-18.4 kcal mol -1 , the extreme values corresponding to derivatives 1 (R=Me) and 4 (R=Bu t ), respectively. NOE and LIS measurements indicated that the Z atropisomer is more stable than the E but that the absence of the methyl group at position 2 of the naphthalene moiety reverses this trend, rendering E more stable than Z. Solid-state NMR and Z-ray diffraction of 4 established that only the more stable atropisomer (Z) is present in the crystalline state
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Casarini D. et al. Conformational studies by dynamic NMR. 50. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution // Journal of Organic Chemistry. 1993. Vol. 58. No. 21. pp. 5674-5682.
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Gasparrini F., Macciantelli D., Villani C. Conformational studies by dynamic NMR. 50. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution // Journal of Organic Chemistry. 1993. Vol. 58. No. 21. pp. 5674-5682.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo00073a028
UR - https://doi.org/10.1021/jo00073a028
TI - Conformational studies by dynamic NMR. 50. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution
T2 - Journal of Organic Chemistry
AU - Gasparrini, F.
AU - Macciantelli, D.
AU - Villani, Claudio
PY - 1993
DA - 1993/10/01
PB - American Chemical Society (ACS)
SP - 5674-5682
IS - 21
VL - 58
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{1993_Casarini,
author = {F. Gasparrini and D. Macciantelli and Claudio Villani},
title = {Conformational studies by dynamic NMR. 50. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution},
journal = {Journal of Organic Chemistry},
year = {1993},
volume = {58},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/jo00073a028},
number = {21},
pages = {5674--5682},
doi = {10.1021/jo00073a028}
}
Cite this
MLA
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Casarini, Daniele, et al. “Conformational studies by dynamic NMR. 50. Atropisomerism in hindered naphthyl sulfoxides: structure, stereodynamics, and chiral resolution.” Journal of Organic Chemistry, vol. 58, no. 21, Oct. 1993, pp. 5674-5682. https://doi.org/10.1021/jo00073a028.