The structure, stability, and CID pattern of proton-bound homochiral and heterochiral complexes, formed in the gas phase by the combination of two molecules of a chiral macrocyclic tetra-amide and an amine B, i.e. CH(3)NH(2), (CH(3))(2)NH, or (S)-(-)-1-phenylethylamine, have been examined by ESI-ITMS-CID mass spectrometry. With B = CH(3)NH(2), the CID pattern is characterized by the predominant loss of B, accompanied by a much less extensive release of one tetra-amide molecule. With (S)-(-)-1-phenylethylamine, loss of a tetra- amide molecule efficiently competes with loss of B. Finally, with (CH(3))(2)NH, loss of a tetra- amide molecule predominates over loss of B. No appreciable isotope and chiral guest configuration effects have been detected in the fragmentation of the homochiral complexes. A distinct configurational effect has been appreciated in the CID of the homo- and the heterochiral complexes with all amines used. The results of this study have been discussed in the light of semi-empirical computational evidence. The differences in the CID patterns of the homo- and the heterochiral complexes have been rationalized in terms of structural factors and of the basicity of amine B.

GAS-PHASE STRUCTURE AND RELATIVE STABILITY OF PROTON-BOUND HOMO- AND HETEROCHIRAL CLUSTERS OF TETRA-AMIDE MACROCYCLES WITH AMINES / Fraschetti, Caterina; Pierini, Marco; Villani, Claudio; Gasparrini, Francesco; Filippi, Antonello; Speranza, Maurizio. - In: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS. - ISSN 0010-0765. - STAMPA. - 74:2(2009), pp. 275-297. [10.1135/cccc2008155]

GAS-PHASE STRUCTURE AND RELATIVE STABILITY OF PROTON-BOUND HOMO- AND HETEROCHIRAL CLUSTERS OF TETRA-AMIDE MACROCYCLES WITH AMINES

FRASCHETTI, CATERINA;PIERINI, MARCO;VILLANI, Claudio;GASPARRINI, Francesco;FILIPPI, Antonello;SPERANZA, Maurizio
2009

Abstract

The structure, stability, and CID pattern of proton-bound homochiral and heterochiral complexes, formed in the gas phase by the combination of two molecules of a chiral macrocyclic tetra-amide and an amine B, i.e. CH(3)NH(2), (CH(3))(2)NH, or (S)-(-)-1-phenylethylamine, have been examined by ESI-ITMS-CID mass spectrometry. With B = CH(3)NH(2), the CID pattern is characterized by the predominant loss of B, accompanied by a much less extensive release of one tetra-amide molecule. With (S)-(-)-1-phenylethylamine, loss of a tetra- amide molecule efficiently competes with loss of B. Finally, with (CH(3))(2)NH, loss of a tetra- amide molecule predominates over loss of B. No appreciable isotope and chiral guest configuration effects have been detected in the fragmentation of the homochiral complexes. A distinct configurational effect has been appreciated in the CID of the homo- and the heterochiral complexes with all amines used. The results of this study have been discussed in the light of semi-empirical computational evidence. The differences in the CID patterns of the homo- and the heterochiral complexes have been rationalized in terms of structural factors and of the basicity of amine B.
2009
amines; chiral clusters; collision-induced dissociation; diastereoselectivity; gas-phase chiral recognition; mass spectrometry; supramolecular isomers
01 Pubblicazione su rivista::01a Articolo in rivista
GAS-PHASE STRUCTURE AND RELATIVE STABILITY OF PROTON-BOUND HOMO- AND HETEROCHIRAL CLUSTERS OF TETRA-AMIDE MACROCYCLES WITH AMINES / Fraschetti, Caterina; Pierini, Marco; Villani, Claudio; Gasparrini, Francesco; Filippi, Antonello; Speranza, Maurizio. - In: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS. - ISSN 0010-0765. - STAMPA. - 74:2(2009), pp. 275-297. [10.1135/cccc2008155]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/229089
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