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Experimental and DFT Studies of the Electron‐Withdrawing Ability of Perfluoroalkyl (R F ) Groups: Electron Affinities of PAH(R F ) n Increase Significantly with Increasing R F Chain Length
Author(s) -
San Long K.,
Spisak Sarah N.,
Dubceac Cristina,
Deng Shihu H M.,
Kuvychko Igor V.,
Petrukhina Marina A.,
Wang XueBin,
Popov Alexey A.,
Strauss Steven H.,
Boltalina Olga V.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704868
Subject(s) - affinities , polar effect , electron , chemistry , stereochemistry , medicinal chemistry , physics , nuclear physics
Two series of aromatic compounds with perfluoroalkyl (R F ) groups of increasing length, 1,3,5,7‐naphthalene(R F ) 4 and 1,3,5,7,9‐corannulene(R F ) 5 , have been prepared and their electronic properties studied by low‐temperature photoelectron spectroscopy (PES) (for gas‐phase electron affinity measurements). These and many related compounds were also studied by DFT calculations. The data demonstrate unambiguously that the electron‐withdrawing ability of R F substituents increases significantly and uniformly from CF 3 to C 2 F 5 to n ‐C 3 F 7 to n ‐C 4 F 9 .