Bent aromatic rings in naphthalene derivatives

Peter R. Ashton; George R. Brown; Alan J. Foubister; Diane R. Smith; Neil Spencer; J. Fraser Stoddart; David J. Williams

doi:10.1016/S0040-4039(00)61424-7

Bent aromatic rings in naphthalene derivatives

Peter R. Ashton^*, George R. Brown, Alan J. Foubister, Diane R. Smith, Neil Spencer, J. Fraser Stoddart, David J. Williams

^*Corresponding author for this work

Chemistry

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

8 Scopus citations

Abstract

X-Ray crystallography and dynamic ¹H NMR spectroscopy have revealed that 1,4,5,8-tetramethyl-, 1-bromomethyl-4,5,8-trimethyl-, and 1,8-bis(bromomethyl)-4,5-dimethyl-2,3,6,7-tetrabromonaphthalene - 3, 4, and 5, respectively - have severely distorted naphthalene nuclei in the solid state that also correspond to the gross conformations that occupy appreciable (ΔG‡∼16 kcal mol^-1) energy wells in the solution state.

Original language	English (US)
Pages (from-to)	8333-8336
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4039(00)61424-7
State	Published - Dec 17 1993

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{e530ec1c3f894ea8abf9684246a8e811,

title = "Bent aromatic rings in naphthalene derivatives",

abstract = "X-Ray crystallography and dynamic 1H NMR spectroscopy have revealed that 1,4,5,8-tetramethyl-, 1-bromomethyl-4,5,8-trimethyl-, and 1,8-bis(bromomethyl)-4,5-dimethyl-2,3,6,7-tetrabromonaphthalene - 3, 4, and 5, respectively - have severely distorted naphthalene nuclei in the solid state that also correspond to the gross conformations that occupy appreciable (ΔG‡∼16 kcal mol-1) energy wells in the solution state.",

author = "Ashton, {Peter R.} and Brown, {George R.} and Foubister, {Alan J.} and Smith, {Diane R.} and Neil Spencer and Stoddart, {J. Fraser} and Williams, {David J.}",

note = "Funding Information: Acknowledgement. We are grateful to the Science and Engineering Research Council in the UK and ZENECA Pharmaceuticals for the support of this research programme.",

year = "1993",

month = dec,

day = "17",

doi = "10.1016/S0040-4039(00)61424-7",

language = "English (US)",

volume = "34",

pages = "8333--8336",

journal = "Tetrahedron Letters",

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number = "51",

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TY - JOUR

T1 - Bent aromatic rings in naphthalene derivatives

AU - Ashton, Peter R.

AU - Brown, George R.

AU - Foubister, Alan J.

AU - Smith, Diane R.

AU - Spencer, Neil

AU - Stoddart, J. Fraser

AU - Williams, David J.

N1 - Funding Information: Acknowledgement. We are grateful to the Science and Engineering Research Council in the UK and ZENECA Pharmaceuticals for the support of this research programme.

PY - 1993/12/17

Y1 - 1993/12/17

N2 - X-Ray crystallography and dynamic 1H NMR spectroscopy have revealed that 1,4,5,8-tetramethyl-, 1-bromomethyl-4,5,8-trimethyl-, and 1,8-bis(bromomethyl)-4,5-dimethyl-2,3,6,7-tetrabromonaphthalene - 3, 4, and 5, respectively - have severely distorted naphthalene nuclei in the solid state that also correspond to the gross conformations that occupy appreciable (ΔG‡∼16 kcal mol-1) energy wells in the solution state.

AB - X-Ray crystallography and dynamic 1H NMR spectroscopy have revealed that 1,4,5,8-tetramethyl-, 1-bromomethyl-4,5,8-trimethyl-, and 1,8-bis(bromomethyl)-4,5-dimethyl-2,3,6,7-tetrabromonaphthalene - 3, 4, and 5, respectively - have severely distorted naphthalene nuclei in the solid state that also correspond to the gross conformations that occupy appreciable (ΔG‡∼16 kcal mol-1) energy wells in the solution state.

UR - http://www.scopus.com/inward/record.url?scp=0027759737&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027759737&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)61424-7

DO - 10.1016/S0040-4039(00)61424-7

M3 - Article

AN - SCOPUS:0027759737

VL - 34

SP - 8333

EP - 8336

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 51

ER -

Bent aromatic rings in naphthalene derivatives

Abstract

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