Cyclopropenyl Cation. Synthesis and Characterization

Ronald Breslow; John Taylor Groves

doi:10.1021/ja00707a040

Cyclopropenyl Cation. Synthesis and Characterization

Ronald Breslow, John Taylor Groves

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

118 Scopus citations

Abstract

Three salts of cyclopropenyl cation (I) have been prepared from 3-chlorocyclopropene. The nmr spectrum of the cation is consistent with expectations, and the infrared spectrum has only four bands which have been assigned to the four allowed modes for a molecule with D_3h symmetry. The PK_R+ of I was determined to be –7.4 ± 0.1 by an nmr method. Comparison with an estimated pK_R+ for allyl cation shows that I is 18 kcal/mole more stabilized. This compares well with a gas-phase value of 17–18 kcal/mole determined from appearance potentials.

Original language	English (US)
Pages (from-to)	984-987
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	92
Issue number	4
DOIs	https://doi.org/10.1021/ja00707a040
State	Published - Feb 1 1970

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja00707a040

Cite this

@article{52589913b7d24dbf9afd9b384ebed3b1,

title = "Cyclopropenyl Cation. Synthesis and Characterization",

abstract = "Three salts of cyclopropenyl cation (I) have been prepared from 3-chlorocyclopropene. The nmr spectrum of the cation is consistent with expectations, and the infrared spectrum has only four bands which have been assigned to the four allowed modes for a molecule with D3h symmetry. The PKR+ of I was determined to be –7.4 ± 0.1 by an nmr method. Comparison with an estimated pKR+ for allyl cation shows that I is 18 kcal/mole more stabilized. This compares well with a gas-phase value of 17–18 kcal/mole determined from appearance potentials.",

author = "Ronald Breslow and Groves, {John Taylor}",

year = "1970",

month = feb,

day = "1",

doi = "10.1021/ja00707a040",

language = "English (US)",

volume = "92",

pages = "984--987",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Cyclopropenyl Cation. Synthesis and Characterization

AU - Breslow, Ronald

AU - Groves, John Taylor

PY - 1970/2/1

Y1 - 1970/2/1

N2 - Three salts of cyclopropenyl cation (I) have been prepared from 3-chlorocyclopropene. The nmr spectrum of the cation is consistent with expectations, and the infrared spectrum has only four bands which have been assigned to the four allowed modes for a molecule with D3h symmetry. The PKR+ of I was determined to be –7.4 ± 0.1 by an nmr method. Comparison with an estimated pKR+ for allyl cation shows that I is 18 kcal/mole more stabilized. This compares well with a gas-phase value of 17–18 kcal/mole determined from appearance potentials.

AB - Three salts of cyclopropenyl cation (I) have been prepared from 3-chlorocyclopropene. The nmr spectrum of the cation is consistent with expectations, and the infrared spectrum has only four bands which have been assigned to the four allowed modes for a molecule with D3h symmetry. The PKR+ of I was determined to be –7.4 ± 0.1 by an nmr method. Comparison with an estimated pKR+ for allyl cation shows that I is 18 kcal/mole more stabilized. This compares well with a gas-phase value of 17–18 kcal/mole determined from appearance potentials.

UR - http://www.scopus.com/inward/record.url?scp=33947296578&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33947296578&partnerID=8YFLogxK

U2 - 10.1021/ja00707a040

DO - 10.1021/ja00707a040

M3 - Article

AN - SCOPUS:33947296578

SN - 0002-7863

VL - 92

SP - 984

EP - 987

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 4

ER -

Cyclopropenyl Cation. Synthesis and Characterization

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this