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",

publisher = "Elsevier B.V.",

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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

UR - https://www.scopus.com/pages/publications/84907291626

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

Access to Document

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