Structural Chemistry

, Volume 11, Issue 6, pp 335–340 | Cite as

Basicity and Proton Transfer in Proton Sponges and Related Compounds: An Ab Initio Study

  • Ibon Alkorta
  • José Elguero

Abstract

Theoretical calculations at the B3LYP/6-31G* level were carried out on a family of 1,8-diR-naphthalenes, which include the proton sponge (1,8-bisdimethylaminonaphthalene, R = NMe2) and other substituents (R = NH2, R = OH, R = CH3, R = F). Their basicity was compared with that of the corresponding monosubstituted benzenes. The dianion of 1,8-dihydroxynaphthalene should be a compound of extraordinary high basicity. The barriers to proton transfer, geometry, and density at the bond critical point of the hydrogen bond have been calculated and compared with experimental data when available.

Proton sponges proton transfer basicity monosubstituted benzenes LBHB 

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Copyright information

© Plenum Publishing Corporation 2000

Authors and Affiliations

  • Ibon Alkorta
    • 1
  • José Elguero
    • 2
  1. 1.Instituto Química Médica, CSICMadridSpain
  2. 2.Instituto Química Médica, CSICMadridSpain

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