Core protonation of meso-tetraphenylporphyrin with tetrafluoroboric acid:: unusual water-mediated hydrogen bonding of H4tpp2+ to the counterion

被引：20

作者：

Rayati, Saeed ^{[1
]}

Zakavi, Saeed ^{[2
]}

Ghaemi, Akbar ^{[1
]}

Carroll, Patrick J. ^{[3
]}

机构：

[1] Zanjan Univ, Dept Chem, Fac Sci, Zanjan 45195313, Iran

[2] Damghan Univ Basic Sci, Dept Chem, Damghan 3671641167, Iran

[3] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 04期

关键词：

meso-tetraphenylporphyrin; dication; hydrogen bonding; saddled conformation; HBF4;

D O I：

10.1016/j.tetlet.2007.11.140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Protonation of meso-tetraphenylporphyrin (H(2)tpp) with tetrafluoroboric acid gives a hydrated porphyrin dication of the formula [H(4)tpp](BF4)(2)center dot 2H(2)O-CHCl3, in which the saddled [H(4)tpp](2+) moiety is hydrogen bonded to the counterions through the two water molecules. Apparently, the formation of this unusual porphyrin diacid serves to optimize the hydrogen bonding. Rather than the tetrafluoroborate ion hydrogen bonding to the two N-H's of [H(4)tpp](2+), the water molecules interact with [H(4)tpp](2+) and then with the BF4- counterions. The average pyrrole tilt angle with the N4 plane is 23.37 degrees and an essentially saddled porphyrin core structure. with insignificant ruffling of the porphyrin core, is observed. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：664 / 667

页数：4

共 3 条

[1] SYNTHESIS AND STRUCTURE OF A COBALT(I) MESO-TETRAPHENYLPORPHYRIN COMPLEX, "[COI(TPP)][K-SUBSET-OF-222]4CL3.H2O
DOPPELT, P
FISCHER, J
WEISS, R
INORGANIC CHEMISTRY, 1984, 23 (19) : 2958 - 2962
[2] Effects of porphyrin core saddling, meso-phenyl twisting and counterions on the optical properties of meso-tetraphenylporphyrin diacids:: The [H4TPP](X)2 (X = F, Cl, B, I) series as a case study
Rosa, A
Ricciardi, G
Baerends, EJ
Romeo, A
Scolaro, LM
JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (51): : 11468 - 11482
[3] Hydrogen Bonding and Water Networks in a 3-D Coordination Polymer [Ag(bpp)]2(BDC)•8H2O (bpp=1,3-Bis(4-pyridyl)propane; BDC = Benzene-1,4-dicarboxylic acid)
Wang, Chong-Chen
Wang, Peng
ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (04) : 1449 - 1452

← 1 →