Structural analysis of 2,6‐[bis(alkyloxy)methyl]‐phenyltin derivatives using electrospray ionization mass spectrometry

Abstract

Electrospray ionization (ESI) mass spectrometry was applied to the structural analysis of 23 2,6-[bis(alkyloxy)methyl]phenyltin(IV) derivatives. The mass spectra were measured in both polarity modes and multistage tandem mass spectrometric (MS(n)) measurements were performed on the ion trap analyser for positively charged tin-containing ions. The sum of complementary ions observed in the positive-ion mode (i.e. [M-R(3)](+) ion) and in the negative-ion mode (i.e. [R(3)](-) ion) permits molecular mass determination in spite of the fact that the molecular adducts were often missing even in the first-order mass spectra. The subsequent fragmentation of [M-R(3)](+) ions studied by MS(n) and the correlation of observed fragment ions with the expected structures of synthesized organotin(IV) compounds allowed us to understand the fragmentation behaviour and the mechanism of the ion formation for studied compounds. The typical neutral losses are alkenes, alcohols and aldehydes. The fragmentation pattern of one selected compound was supported by MS(n) measurements of an isotopically labelled analogue to confirm unusual ion-molecule reactions of some fragment ions with water in the ion trap.

Structural study of bis(triorganotin(IV)) esters of 4-ketopimelic acid

“…The typical feature of ESI mass spectra of organotin carboxylates consists in the cleavage of the most labile Sn-O bond in the molecules yielding two complementary ions, where the cationic part (''Cat'') of the molecule is measured in the positive-ion mode and the anionic part (''An'') in the negativeion mode [9]. The cationic part [SnR 3 ] + (base peak for R = Me) and subsequent fragment ions [HSnR 2 ] + and [H 2 SnR] + (base peak for R = Bz) were observed in the first-order positive ESI mass spectra.…”

Structure and properties of double-C,N-chelated tri- and diorganotin(IV) halides

“…In the early studies of organotin compounds 24 the typical feature of the ESI mass spectra is the cleavage of the most labile bond in the molecules to yield two complementary ions, where the cationic part of the molecule can be measured in the positiveion mode and the anionic part in the negative-ion mode. When the tin-halogen bond was present in the structure the bond was primarily cleaved and …”

Synthesis, crystal structures, cytotoxicity and qualitative structure–activity relationship (QSAR) of cis-bis{5-[(E)-2-(aryl)-1-diazenyl]quinolinolato}di-n-butyltin(IV) complexes, Bu2Sn(L)2

“…[MÀL] + or [MÀCl] + , and the anionic part in the negative-ion mass spectra, i.e. [L] À [17,18,61]. The ion [Cl] À cannot be observed in the spectra because the m/z value of 35 is outside the instrument scan range.…”