Insight into the intramolecular interactions of trans-2-azidocycloalk-3-en-1-ols and trans-2-azidocycloalk-3-en-1-yl acetates: A theoretical study
Özet
In this study, dedicated to Prof. Dr. Yasar Sutbeyaz (1950e2016), intramolecular interactions in (1S(R),2S(R))-2-azidocycloalk-3-en-1-ols and (1S(R),2S(R))-2-azidocycloalk-3-en-1-yl acetates consisting of six-to eight-membered rings were investigated by molecular spectroscopy and density functional theory calculations including three different functional levels, B3LYP, M06-2X and omega B97XD with the 6-31 +G(d,p) basis set. These allylic azides stabilized by intramolecular OH center dot center dot center dot N and CH center dot center dot center dot N interactions did not cause the Winstein rearrangement known as the 1,3-allylic azide rearrangement or [3,3]-sigmatropic rearrangement. The results of the structural parameters, relative total energies, natural bond orbital analysis of donor-acceptor interactions and charges on the atoms support why the Winstein rearrangement does not occur. The quantum chemical reactivity identifiers and molecular electrostatic potential were analyzed using the M062X/6-31+G(d,p) basis set. (c) 2021 Elsevier Ltd. All rights reserved.
Anahtar kelimeler
Atıf için künye
Çetinkaya, Y., Maraş, A., & Göksu, S. (2021). Insight into the intramolecular interactions of trans-2-azidocycloalk-3-en-1-ols and trans-2-azidocycloalk-3-en-1-yl acetates: A theoretical study. TETRAHEDRON, 92. https://doi.org/10.1016/j.tet.2021.132272
BibTeX
@article{cetinkaya2021-72155,
author = {Çetinkaya, Yasin and Maraş, Ahmet and Göksu, Süleyman},
title = {Insight into the intramolecular interactions of trans-2-azidocycloalk-3-en-1-ols and trans-2-azidocycloalk-3-en-1-yl acetates: A theoretical study},
journal = {TETRAHEDRON},
year = {2021},
volume = {92},
issn = {0040-4020},
doi = {10.1016/j.tet.2021.132272},
url = {https://akademik.atauni.edu.tr/yayinlar/72155-insight-into-the-intramolecular-interactions-of-trans-2-azidocycloalk-3-en-1-ols}
}