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Gas‐Phase Basicities of Furan Compounds. The Role of Alkyl Substitution on Proton Affinity and on the Site of Protonation
Author(s) -
Houriet Raymond,
Rolli Eric,
Bouchoux Guy,
Hoppilliard Yannick
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680729
Subject(s) - chemistry , protonation , proton affinity , furan , alkyl , ion cyclotron resonance , electrophilic substitution , electrophile , proton , electrophilic aromatic substitution , computational chemistry , reactivity (psychology) , ion , medicinal chemistry , photochemistry , organic chemistry , catalysis , medicine , cyclotron , physics , alternative medicine , pathology , quantum mechanics
The gas‐phase protonation of alkyl‐substituted furan compounds is investigated in equilibrium proton‐transfer reactions conducted in an ion cyclotron resonance (ICR) spectrometer. From the effects of substituents on the stability of protonated species, it is concluded that protonation of the majority of these systems occurs specifically on the C(α)‐atom to form carbenium ions. Parallel MO calculations performed on different structures of the products reinforce the experimental conclusions and provide energy values for the less stable structures. The solution reactivity of these compounds towards electrophilic agents and NMR spectra of protonated species obtained in strong acidic media have been investigated.