Electron and chemical ionization mass spectrometry in stereochemical differentiation of some 1,3‐amino alcohols

Tuula Partanen, Pirjo Vainiotalo, G. Stájer, G. Bernáth, Kalevi Pihlaja

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Mass spectral fragmentations of two cyclopentane, eight cyclohexane and four norbornane/one 1,3‐amino alcohols were studied under electron ionization (EI) by low‐resolution, high‐resolution, metastable ion analysis and collision‐induced dissociation (CID) techniques. All stereoisomeric compounds gave rise to identical 70 eV EI mass spectra. However, the spectra of positional isomers clearly differed. The main fragmentation pathway for the saturated compounds began as an α‐cleavage reaction with respect to the nitrogen atom. For the norbornene compounds a retro‐Diels—Alder reaction was favoured. Relative to the aminomethyl‐substituted compounds the fragmentation patterns for the compounds having the amino group connected directly to the ring were more complicated. The chemical ionization (CI) mass spectra were recorded using ammonia, isobutane, methane, dichloromethane and acetone as reagent gas. From the norbornane/One compounds the di‐exo isomers decomposed more easily than the di‐endo isomers with most of the reagent gases used. Differences between stereoisomers were observed directly only under methane CI. The decomposition products of the [M + H]+ ions generated under ammonia and isobutane CI were studies by recording their CID mass spectra. These spectra allowed the differentiation of the stereoisomers, at least to some extent.

Original languageEnglish
Pages (from-to)126-132
Number of pages7
JournalOrganic Mass Spectrometry
Volume29
Issue number3
DOIs
Publication statusPublished - 1994

Fingerprint

Norbornanes
Butanes
Stereoisomerism
Methane
Ammonia
Ionization
Mass spectrometry
Mass Spectrometry
alcohols
Alcohols
mass spectroscopy
Gases
Electrons
Ions
Cyclopentanes
ionization
Isomers
Methylene Chloride
mass spectra
Acetone

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Instrumentation

Cite this

Electron and chemical ionization mass spectrometry in stereochemical differentiation of some 1,3‐amino alcohols. / Partanen, Tuula; Vainiotalo, Pirjo; Stájer, G.; Bernáth, G.; Pihlaja, Kalevi.

In: Organic Mass Spectrometry, Vol. 29, No. 3, 1994, p. 126-132.

Research output: Contribution to journalArticle

@article{a5c53d3fb85243409c8e4d4743a9d104,
title = "Electron and chemical ionization mass spectrometry in stereochemical differentiation of some 1,3‐amino alcohols",
abstract = "Mass spectral fragmentations of two cyclopentane, eight cyclohexane and four norbornane/one 1,3‐amino alcohols were studied under electron ionization (EI) by low‐resolution, high‐resolution, metastable ion analysis and collision‐induced dissociation (CID) techniques. All stereoisomeric compounds gave rise to identical 70 eV EI mass spectra. However, the spectra of positional isomers clearly differed. The main fragmentation pathway for the saturated compounds began as an α‐cleavage reaction with respect to the nitrogen atom. For the norbornene compounds a retro‐Diels—Alder reaction was favoured. Relative to the aminomethyl‐substituted compounds the fragmentation patterns for the compounds having the amino group connected directly to the ring were more complicated. The chemical ionization (CI) mass spectra were recorded using ammonia, isobutane, methane, dichloromethane and acetone as reagent gas. From the norbornane/One compounds the di‐exo isomers decomposed more easily than the di‐endo isomers with most of the reagent gases used. Differences between stereoisomers were observed directly only under methane CI. The decomposition products of the [M + H]+ ions generated under ammonia and isobutane CI were studies by recording their CID mass spectra. These spectra allowed the differentiation of the stereoisomers, at least to some extent.",
author = "Tuula Partanen and Pirjo Vainiotalo and G. St{\'a}jer and G. Bern{\'a}th and Kalevi Pihlaja",
year = "1994",
doi = "10.1002/oms.1210290303",
language = "English",
volume = "29",
pages = "126--132",
journal = "Biological Mass Spectrometry",
issn = "1076-5174",
publisher = "John Wiley and Sons Ltd",
number = "3",

}

TY - JOUR

T1 - Electron and chemical ionization mass spectrometry in stereochemical differentiation of some 1,3‐amino alcohols

AU - Partanen, Tuula

AU - Vainiotalo, Pirjo

AU - Stájer, G.

AU - Bernáth, G.

AU - Pihlaja, Kalevi

PY - 1994

Y1 - 1994

N2 - Mass spectral fragmentations of two cyclopentane, eight cyclohexane and four norbornane/one 1,3‐amino alcohols were studied under electron ionization (EI) by low‐resolution, high‐resolution, metastable ion analysis and collision‐induced dissociation (CID) techniques. All stereoisomeric compounds gave rise to identical 70 eV EI mass spectra. However, the spectra of positional isomers clearly differed. The main fragmentation pathway for the saturated compounds began as an α‐cleavage reaction with respect to the nitrogen atom. For the norbornene compounds a retro‐Diels—Alder reaction was favoured. Relative to the aminomethyl‐substituted compounds the fragmentation patterns for the compounds having the amino group connected directly to the ring were more complicated. The chemical ionization (CI) mass spectra were recorded using ammonia, isobutane, methane, dichloromethane and acetone as reagent gas. From the norbornane/One compounds the di‐exo isomers decomposed more easily than the di‐endo isomers with most of the reagent gases used. Differences between stereoisomers were observed directly only under methane CI. The decomposition products of the [M + H]+ ions generated under ammonia and isobutane CI were studies by recording their CID mass spectra. These spectra allowed the differentiation of the stereoisomers, at least to some extent.

AB - Mass spectral fragmentations of two cyclopentane, eight cyclohexane and four norbornane/one 1,3‐amino alcohols were studied under electron ionization (EI) by low‐resolution, high‐resolution, metastable ion analysis and collision‐induced dissociation (CID) techniques. All stereoisomeric compounds gave rise to identical 70 eV EI mass spectra. However, the spectra of positional isomers clearly differed. The main fragmentation pathway for the saturated compounds began as an α‐cleavage reaction with respect to the nitrogen atom. For the norbornene compounds a retro‐Diels—Alder reaction was favoured. Relative to the aminomethyl‐substituted compounds the fragmentation patterns for the compounds having the amino group connected directly to the ring were more complicated. The chemical ionization (CI) mass spectra were recorded using ammonia, isobutane, methane, dichloromethane and acetone as reagent gas. From the norbornane/One compounds the di‐exo isomers decomposed more easily than the di‐endo isomers with most of the reagent gases used. Differences between stereoisomers were observed directly only under methane CI. The decomposition products of the [M + H]+ ions generated under ammonia and isobutane CI were studies by recording their CID mass spectra. These spectra allowed the differentiation of the stereoisomers, at least to some extent.

UR - http://www.scopus.com/inward/record.url?scp=84989030550&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84989030550&partnerID=8YFLogxK

U2 - 10.1002/oms.1210290303

DO - 10.1002/oms.1210290303

M3 - Article

AN - SCOPUS:84989030550

VL - 29

SP - 126

EP - 132

JO - Biological Mass Spectrometry

JF - Biological Mass Spectrometry

SN - 1076-5174

IS - 3

ER -