Stereoselectivity in complexation of primary alkylammonium cations by the diastereotopic faces of chiral asymmetric crowns

Dale A. Laidler; J. Fraser Stoddart

doi:10.1039/C39770000481

Stereoselectivity in complexation of primary alkylammonium cations by the diastereotopic faces of chiral asymmetric crowns

Dale A. Laidler, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

42 Scopus citations

Abstract

The temperature-dependent ¹H n.m.r. spectra of the 1:1 complexes formed between crowns D-(1), DD-(2), D-(3), and DD-(4) and primary alkylammonium cations in solution are interpreted in terms of equilibria involving diastereoisomeric complexes of (i) similar strengths in the case of the galacto-crowns D-(1) and DD-(2) and (ii) dissimilar strengths in the case of the gluco-crowns D-(3) and DD-(4) where a secondary interaction of a dipole-induced dipole type appears to be responsible for the stereoselectivity.

Original language	English (US)
Pages (from-to)	481-483
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	14
DOIs	https://doi.org/10.1039/C39770000481
State	Published - 1977

ASJC Scopus subject areas

Molecular Medicine

Access to Document

10.1039/C39770000481

Cite this

@article{7c9c95a69f12473ebeee813f9103e213,

title = "Stereoselectivity in complexation of primary alkylammonium cations by the diastereotopic faces of chiral asymmetric crowns",

abstract = "The temperature-dependent 1H n.m.r. spectra of the 1:1 complexes formed between crowns D-(1), DD-(2), D-(3), and DD-(4) and primary alkylammonium cations in solution are interpreted in terms of equilibria involving diastereoisomeric complexes of (i) similar strengths in the case of the galacto-crowns D-(1) and DD-(2) and (ii) dissimilar strengths in the case of the gluco-crowns D-(3) and DD-(4) where a secondary interaction of a dipole-induced dipole type appears to be responsible for the stereoselectivity.",

author = "Laidler, {Dale A.} and Stoddart, {J. Fraser}",

year = "1977",

doi = "10.1039/C39770000481",

language = "English (US)",

pages = "481--483",

journal = "Journal of the Chemical Society, Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "14",

}

TY - JOUR

T1 - Stereoselectivity in complexation of primary alkylammonium cations by the diastereotopic faces of chiral asymmetric crowns

AU - Laidler, Dale A.

AU - Stoddart, J. Fraser

PY - 1977

Y1 - 1977

N2 - The temperature-dependent 1H n.m.r. spectra of the 1:1 complexes formed between crowns D-(1), DD-(2), D-(3), and DD-(4) and primary alkylammonium cations in solution are interpreted in terms of equilibria involving diastereoisomeric complexes of (i) similar strengths in the case of the galacto-crowns D-(1) and DD-(2) and (ii) dissimilar strengths in the case of the gluco-crowns D-(3) and DD-(4) where a secondary interaction of a dipole-induced dipole type appears to be responsible for the stereoselectivity.

AB - The temperature-dependent 1H n.m.r. spectra of the 1:1 complexes formed between crowns D-(1), DD-(2), D-(3), and DD-(4) and primary alkylammonium cations in solution are interpreted in terms of equilibria involving diastereoisomeric complexes of (i) similar strengths in the case of the galacto-crowns D-(1) and DD-(2) and (ii) dissimilar strengths in the case of the gluco-crowns D-(3) and DD-(4) where a secondary interaction of a dipole-induced dipole type appears to be responsible for the stereoselectivity.

UR - http://www.scopus.com/inward/record.url?scp=37049096560&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049096560&partnerID=8YFLogxK

U2 - 10.1039/C39770000481

DO - 10.1039/C39770000481

M3 - Article

AN - SCOPUS:37049096560

SN - 0022-4936

SP - 481

EP - 483

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 14

ER -

Stereoselectivity in complexation of primary alkylammonium cations by the diastereotopic faces of chiral asymmetric crowns

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this