Substituent effects on the13C and17O NMR, IR, and UV spectral parameters for propynals

A. S. Medvedeva; O. I. Margorskaya; I. D. Kalikhman; N. I. Golovanova; N. I. Shergina; N. S. Vyazankin

doi:10.1007/BF00957419

Substituent effects on the¹³C and¹⁷O NMR, IR, and UV spectral parameters for propynals

A. S. Medvedeva, O. I. Margorskaya, I. D. Kalikhman, N. I. Golovanova, N. I. Shergina, N. S. Vyazankin

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

2 Scopus citations

Abstract

Trialkylsilyl(germanyl)propynals show a lower triple bond polarization compared with their carbon analogs because of the electron acceptor effects of the R substituents and the aldehyde group. This increases the inertness of the C≡C bond towards nucleophiles (RSH, R₂NH) and lowers the regioselectivity of dipolar attack. Lowering the relative basicity of the substituted propynals decreases the integrated intensity of the C=0 absorption band and shifts the δ¹⁷O signal to low field.

Original language	English
Pages (from-to)	246-249
Number of pages	4
Journal	Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume	37
Issue number	2
DOIs	https://doi.org/10.1007/BF00957419
State	Published - 1 Feb 1988
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1007/BF00957419

Cite this

@article{f2492d2e2276423698f67c0a1549c400,

title = "Substituent effects on the13C and17O NMR, IR, and UV spectral parameters for propynals",

abstract = "Trialkylsilyl(germanyl)propynals show a lower triple bond polarization compared with their carbon analogs because of the electron acceptor effects of the R substituents and the aldehyde group. This increases the inertness of the C≡C bond towards nucleophiles (RSH, R2NH) and lowers the regioselectivity of dipolar attack. Lowering the relative basicity of the substituted propynals decreases the integrated intensity of the C=0 absorption band and shifts the δ17O signal to low field.",

author = "Medvedeva, {A. S.} and Margorskaya, {O. I.} and Kalikhman, {I. D.} and Golovanova, {N. I.} and Shergina, {N. I.} and Vyazankin, {N. S.}",

year = "1988",

month = feb,

day = "1",

doi = "10.1007/BF00957419",

language = "English",

volume = "37",

pages = "246--249",

journal = "Bulletin of the Academy of Sciences of the USSR Division of Chemical Science",

issn = "0568-5230",

publisher = "Springer New York",

number = "2",

}

TY - JOUR

T1 - Substituent effects on the13C and17O NMR, IR, and UV spectral parameters for propynals

AU - Medvedeva, A. S.

AU - Margorskaya, O. I.

AU - Kalikhman, I. D.

AU - Golovanova, N. I.

AU - Shergina, N. I.

AU - Vyazankin, N. S.

PY - 1988/2/1

Y1 - 1988/2/1

N2 - Trialkylsilyl(germanyl)propynals show a lower triple bond polarization compared with their carbon analogs because of the electron acceptor effects of the R substituents and the aldehyde group. This increases the inertness of the C≡C bond towards nucleophiles (RSH, R2NH) and lowers the regioselectivity of dipolar attack. Lowering the relative basicity of the substituted propynals decreases the integrated intensity of the C=0 absorption band and shifts the δ17O signal to low field.

AB - Trialkylsilyl(germanyl)propynals show a lower triple bond polarization compared with their carbon analogs because of the electron acceptor effects of the R substituents and the aldehyde group. This increases the inertness of the C≡C bond towards nucleophiles (RSH, R2NH) and lowers the regioselectivity of dipolar attack. Lowering the relative basicity of the substituted propynals decreases the integrated intensity of the C=0 absorption band and shifts the δ17O signal to low field.

UR - http://www.scopus.com/inward/record.url?scp=34249972596&partnerID=8YFLogxK

U2 - 10.1007/BF00957419

DO - 10.1007/BF00957419

M3 - Article

AN - SCOPUS:34249972596

SN - 0568-5230

VL - 37

SP - 246

EP - 249

JO - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science

JF - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science

IS - 2

ER -

Substituent effects on the¹³C and¹⁷O NMR, IR, and UV spectral parameters for propynals

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this