Dissociation of proton-bound complexes and proton affinity of benzamides

Grützmacher H-F, Caltapanides A (1994)
Journal of the American Society for Mass Spectrometry 5(9): 826-836.

Download
OA
Journal Article | Published | English
Author
;
Abstract
Proton-bound heterodimers of substituted benzamides 1-15 and N,N-dimethyl benzamides 16-30, respectively, with a series of reference bases were generated under chemical ionization conditions. Their dissociation into the protonated amide AH+ and protonated reference base BH+ was studied by metastable ion techniques and by collision-induced dissociation (CID) to examine substituent effects on the proton affinity (PA) of the benzamides and to elucidate some aspects of the dissociation dynamics of proton-bound clusters. The PAs of the substituted benzamides were determined by bracketing the amide by a pair of reference bases to give rise to more and less abundant signals of the protonated base in the mass-analyzed ion kinetic energy (MIKE) spectra of the proton-bound heterodimers. The substituent effects observed agree with O-protonation in both the primary and the teritary benzamides. However, the susceptibility of the benzamide to polar substituent effects is remarkably small, which indicates a ''resonance saturation'' of the amide group. The relative abundances of AH+ and BH+ in the MIKE and collisonal activation (CA) mass spectra depend strongly on the pressure of the collision gas during CID, and in certain cases a reversal of the relative abundances with increasing pressure that favors the formation of BH+ from a less basic reference base is observed. Although this effect underlines the limited possibilities of the ''kinetic method'' for PA determination by CID of proton-bound heterodimers, it uncovers important kinetic effects during the dissociation of proton-bound heterodimers and of proton transfer reactions in the gas phase. In the case of the protonated amide clusters, the observed intensity effects in the CA mass spectra are explained by a double-well potential energy surface caused by solvation of the protonated base by the polar amide in the protonated heterodimer.
Publishing Year
ISSN
eISSN
PUB-ID

Cite this

Grützmacher H-F, Caltapanides A. Dissociation of proton-bound complexes and proton affinity of benzamides. Journal of the American Society for Mass Spectrometry. 1994;5(9):826-836.
Grützmacher, H. - F., & Caltapanides, A. (1994). Dissociation of proton-bound complexes and proton affinity of benzamides. Journal of the American Society for Mass Spectrometry, 5(9), 826-836.
Grützmacher, H. - F., and Caltapanides, A. (1994). Dissociation of proton-bound complexes and proton affinity of benzamides. Journal of the American Society for Mass Spectrometry 5, 826-836.
Grützmacher, H.-F., & Caltapanides, A., 1994. Dissociation of proton-bound complexes and proton affinity of benzamides. Journal of the American Society for Mass Spectrometry, 5(9), p 826-836.
H.-F. Grützmacher and A. Caltapanides, “Dissociation of proton-bound complexes and proton affinity of benzamides”, Journal of the American Society for Mass Spectrometry, vol. 5, 1994, pp. 826-836.
Grützmacher, H.-F., Caltapanides, A.: Dissociation of proton-bound complexes and proton affinity of benzamides. Journal of the American Society for Mass Spectrometry. 5, 826-836 (1994).
Grützmacher, Hans-Friedrich, and Caltapanides, Anke. “Dissociation of proton-bound complexes and proton affinity of benzamides”. Journal of the American Society for Mass Spectrometry 5.9 (1994): 826-836.
Main File(s)
File Name
Access Level
OA Open Access

This data publication is cited in the following publications:
This publication cites the following data publications:

4 Citations in Europe PMC

Data provided by Europe PubMed Central.

Dimerization of peptides by calcium ions: investigation of a calcium-binding motif.
Jamalian A, Sneekes EJ, Dekker LJ, Ursem M, Luider TM, Burgers PC., Int J Proteomics 2014(), 2014
PMID: 25295190
Intramolecular transacylation: fragmentation of protonated molecules via ion-neutral complexes in mass spectrometry.
Tu YP, Huang Y, Atsriku C, You Y, Cunniff J., Rapid Commun. Mass Spectrom. 23(13), 2009
PMID: 19504483

Export

0 Marked Publications

Open Data PUB

Web of Science

View record in Web of Science®

Sources

PMID: 24222030
PubMed | Europe PMC

Search this title in

Google Scholar