X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2 '-hydroxyphenyl)-prop-2-en-1-one

Choi, Seunghyun; Kim, YunHye; Park, Bernie Byeonghoon; Park, Suzie; Park, Jonghyun; Ok, Kiwon; Koo, JaeHyung; Jung, Yong Woo; Jeon, Young Ho; Lee, Eun Hee; Lee, Ken S.; Byun, Youngjoo

doi:10.1016/j.molstruc.2014.08.016

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X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2 '-hydroxyphenyl)-prop-2-en-1-one

Choi, Seunghyun;
Kim, YunHye;
Park, Bernie Byeonghoon;
Park, Suzie;
Park, Jonghyun;
... Jung, Yong Woo;
... Jeon, Young Ho;
... Lee, Eun Hee;
... Byun, Youngjoo;
외 3명

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초록

A series of 1-aryl-3-(cyclicamino)-prop-2-en-1-one analogs was synthesized from commercial acetophenones in 2 or 3 steps. Compound 6, (E)-3-(piperidinyl)-1-(2'-hydroxyphenyl)-prop-2-en-1-one, exhibited the unique shape and intensity of the C-sp2-N-CH2 peaks in the H-1 and C-13 NMR spectra. Variable temperature (VT) nuclear magnetic resonance (NMR) and X-ray diffraction (XRD) studies of 6 revealed that the piperidine ring has a lower energy barrier to rotation than the 5-membered pyrrolidine 9 due to the less effective pi electron delocalization along the C-sp2-N bond. (C) 2014 Elsevier B.V. All rights reserved.

키워드

Enaminones; X-ray diffraction; VT-NMR; Flexible rotation; ENAMINONES; BENZOYLACETONE; CONDENSATION; TAUTOMERISM; DERIVATIVES; PRODUCTS

제목: X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2 '-hydroxyphenyl)-prop-2-en-1-one

저자: Choi, Seunghyun; Kim, YunHye; Park, Bernie Byeonghoon; Park, Suzie; Park, Jonghyun; Ok, Kiwon; Koo, JaeHyung; Jung, Yong Woo; Jeon, Young Ho; Lee, Eun Hee; Lee, Ken S.; Byun, Youngjoo

DOI: 10.1016/j.molstruc.2014.08.016

발행일: 2014-11-05

유형: Article

저널명: Journal of Molecular Structure

권: 1076

페이지: 600 ~ 605

언어: ENG

출판사: ELSEVIER

발행국가: 네덜란드

분량: 6 페이지

ISSN: E 1872-8014
P 0022-2860