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

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

doi:10.1016/j.molstruc.2014.08.016

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

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

Department of New Biology

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

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_sp2NCH₂peaks in the ¹H and ¹³C 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 π electron delocalization along the C_sp2N bond.

Original language	English
Pages (from-to)	600-605
Number of pages	6
Journal	Journal of Molecular Structure
Volume	1076
DOIs	https://doi.org/10.1016/j.molstruc.2014.08.016
State	Published - 5 Nov 2014

Bibliographical note

Publisher Copyright:
© 2014 Elsevier B.V. All rights reserved.

Keywords

Enaminones
Flexible rotation
VT-NMR
X-ray diffraction

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10.1016/j.molstruc.2014.08.016

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title = "X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one",

abstract = "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 Csp2NCH2peaks in the 1H and 13C 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 π electron delocalization along the Csp2N bond.",

keywords = "Enaminones, Flexible rotation, VT-NMR, X-ray diffraction",

author = "Seunghyun Choi and Yunhye Kim and Park, {Bernie Byeonghoon} and Suzie Park and Jonghyun Park and Kiwon Ok and Jaehyung Koo and Jung, {Yong Woo} and Jeon, {Young Ho} and Lee, {Eun Hee} and Lee, {Ken S.} and Youngjoo Byun",

year = "2014",

month = nov,

day = "5",

doi = "10.1016/j.molstruc.2014.08.016",

language = "English",

volume = "1076",

pages = "600--605",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

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T1 - X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one

AU - Choi, Seunghyun

AU - Kim, Yunhye

AU - Park, Bernie Byeonghoon

AU - Park, Suzie

AU - Park, Jonghyun

AU - Ok, Kiwon

AU - Koo, Jaehyung

AU - Jung, Yong Woo

AU - Jeon, Young Ho

AU - Lee, Eun Hee

AU - Lee, Ken S.

AU - Byun, Youngjoo

PY - 2014/11/5

Y1 - 2014/11/5

N2 - 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 Csp2NCH2peaks in the 1H and 13C 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 π electron delocalization along the Csp2N bond.

AB - 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 Csp2NCH2peaks in the 1H and 13C 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 π electron delocalization along the Csp2N bond.

KW - Enaminones

KW - Flexible rotation

KW - VT-NMR

KW - X-ray diffraction

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U2 - 10.1016/j.molstruc.2014.08.016

DO - 10.1016/j.molstruc.2014.08.016

M3 - Article

AN - SCOPUS:84907291626

SN - 0022-2860

VL - 1076

SP - 600

EP - 605

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

ER -

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

Abstract

Bibliographical note

Keywords

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