[5]metacyclophanes a spectroscopic and theoretical investigation of structure and conformation

L. A.M. Turkenburg; W. H. de Wolf; F. Bickelhaupt; W. P. Cofino; K. Lammertsma

doi:10.1016/S0040-4039(00)81781-5

[5]metacyclophanes a spectroscopic and theoretical investigation of structure and conformation

L. A.M. Turkenburg, W. H. de Wolf, F. Bickelhaupt, W. P. Cofino, K. Lammertsma

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18 Citations (Scopus)

Abstract

The ¹H NMR spectra of [5]metacyclophane (1a) and of its 8,11-dichloro derivative 1b are reported. 1a Has a rigid conformation A between -50 and +150 °C. Conformation A is also the preferred one (85%) for 1b at -47 °C, but 1b-A is in equilibrium with a second conformer 1b-B, for which spectral parameters can be derived. A and B correspond with two energy minima predicted by MNDO calculations.

Original language	English
Pages (from-to)	1821-1824
Number of pages	4
Journal	Tetrahedron Letters
Volume	24
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(00)81781-5
Publication status	Published - 1983
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "[5]metacyclophanes a spectroscopic and theoretical investigation of structure and conformation",

abstract = "The 1H NMR spectra of [5]metacyclophane (1a) and of its 8,11-dichloro derivative 1b are reported. 1a Has a rigid conformation A between -50 and +150 °C. Conformation A is also the preferred one (85\%) for 1b at -47 °C, but 1b-A is in equilibrium with a second conformer 1b-B, for which spectral parameters can be derived. A and B correspond with two energy minima predicted by MNDO calculations.",

author = "Turkenburg, \{L. A.M.\} and \{de Wolf\}, \{W. H.\} and F. Bickelhaupt and Cofino, \{W. P.\} and K. Lammertsma",

year = "1983",

doi = "10.1016/S0040-4039(00)81781-5",

language = "English",

volume = "24",

pages = "1821--1824",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - [5]metacyclophanes a spectroscopic and theoretical investigation of structure and conformation

AU - Turkenburg, L. A.M.

AU - de Wolf, W. H.

AU - Bickelhaupt, F.

AU - Cofino, W. P.

AU - Lammertsma, K.

PY - 1983

Y1 - 1983

N2 - The 1H NMR spectra of [5]metacyclophane (1a) and of its 8,11-dichloro derivative 1b are reported. 1a Has a rigid conformation A between -50 and +150 °C. Conformation A is also the preferred one (85%) for 1b at -47 °C, but 1b-A is in equilibrium with a second conformer 1b-B, for which spectral parameters can be derived. A and B correspond with two energy minima predicted by MNDO calculations.

AB - The 1H NMR spectra of [5]metacyclophane (1a) and of its 8,11-dichloro derivative 1b are reported. 1a Has a rigid conformation A between -50 and +150 °C. Conformation A is also the preferred one (85%) for 1b at -47 °C, but 1b-A is in equilibrium with a second conformer 1b-B, for which spectral parameters can be derived. A and B correspond with two energy minima predicted by MNDO calculations.

UR - https://www.scopus.com/pages/publications/0001742193

U2 - 10.1016/S0040-4039(00)81781-5

DO - 10.1016/S0040-4039(00)81781-5

M3 - Article

AN - SCOPUS:0001742193

SN - 0040-4039

VL - 24

SP - 1821

EP - 1824

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

[5]metacyclophanes a spectroscopic and theoretical investigation of structure and conformation

Abstract

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