%0 Journal Article %1 ISI:000221417800001 %A Khavasi, HR %A Zahedi, M %A Shahbazian, S %A Safari, N %A Ng, SW %A Mohajer, D %C PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS %D 2004 %I ELSEVIER SCIENCE BV %J CHEMICAL PHYSICS %K BF3; ab acceptor complexes} donor initio methods; {porphine; %N 1 %P 1-7 %R 10.1016/j.chemphys.2004.01.024 %T Prediction of novel complexation of porphine and BF3: Is it a 1 : 1 or 1 : 2 species? %V 301 %X Using various theoretical methods, the complexation of BF3 as a Lewis acid with free base porphine has been investigated. It has been shown that addition of a BF3 molecule to porphine in the first step produces a stable 1:1 complex, and addition of a second BF3 to the 1:1 intermediate forms even more stable 1:2 complex. Generation of both of these complexes are exothermic but formation of the 1:2 adduct is around 2-6 kcal mol(-1) more exothermic than the 1:1 species. Calculation results demonstrate that the most stable species obtained from the interaction of free porphine and BF3 must be trans-por . (BF3)(2) complex, in which BF3 molecules are located on opposite porphine faces, each coordinated to a pyrrolenine nitrogen donor and hydrogen bonded to a pyrrole N-H group. The B-N bond distances of similar to1.6 Angstrom in all the complexes indicate that a strong donor-acceptor interaction takes place between boron atom of BF3 and pyrrolenine nitrogen atom of porphine. Formation of new B-N chemical bonds accompanied by F-H intermolecular hydrogen bonds of similar to1.7 Angstrom length fairly justify molecular complexes stability. This novel complexation and bonding interaction between a single porphine and two BF3 molecules seem to promise the development of a possibly new class of porphine complexes. (C) 2004 Elsevier B.V. All rights reserved.

@article{ISI:000221417800001, abstract = {{Using various theoretical methods, the complexation of BF3 as a Lewis acid with free base porphine has been investigated. It has been shown that addition of a BF3 molecule to porphine in the first step produces a stable 1:1 complex, and addition of a second BF3 to the 1:1 intermediate forms even more stable 1:2 complex. Generation of both of these complexes are exothermic but formation of the 1:2 adduct is around 2-6 kcal mol(-1) more exothermic than the 1:1 species. Calculation results demonstrate that the most stable species obtained from the interaction of free porphine and BF3 must be trans-por . (BF3)(2) complex, in which BF3 molecules are located on opposite porphine faces, each coordinated to a pyrrolenine nitrogen donor and hydrogen bonded to a pyrrole N-H group. The B-N bond distances of similar to1.6 Angstrom in all the complexes indicate that a strong donor-acceptor interaction takes place between boron atom of BF3 and pyrrolenine nitrogen atom of porphine. Formation of new B-N chemical bonds accompanied by F-H intermolecular hydrogen bonds of similar to1.7 Angstrom length fairly justify molecular complexes stability. This novel complexation and bonding interaction between a single porphine and two BF3 molecules seem to promise the development of a possibly new class of porphine complexes. (C) 2004 Elsevier B.V. All rights reserved.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS}}, affiliation = {{Shahid Beheshti Univ, Dept Chem, Tehran, Iran. Shahid Beheshti Univ, Dept Chem, Tehran, Iran. Univ Malaya, Inst Postgrad Studies, Kuala Lumpur 50603, Malaysia. Shiraz Univ, Dept Chem, Shiraz, Iran.}}, author = {Khavasi, HR and Zahedi, M and Shahbazian, S and Safari, N and Ng, SW and Mohajer, D}, author-email = {{m-zahedi@cc.sbu.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/25ac7ad6a7d34179151bc3cc551f8df37/hkhavasi}, cited-references = {{Baker J, 1997, THEOR CHEM ACC, V97, P59, DOI 10.1007/s002140050237. BECKE AD, 1993, J CHEM PHYS, V98, P1372, DOI 10.1063/1.464304. BECKE AD, 1988, PHYS REV A, V38, P3098, DOI 10.1103/PhysRevA.38.3098. BINHLEY TS, 1980, CHEM PHYS LETT, V102, P939. CHEN BML, 1972, J AM CHEM SOC, V94, P4144, DOI 10.1021/ja00767a015. de Visser SP, 2001, J AM CHEM SOC, V123, P3037, DOI 10.1021/ja003544+. DEMONTOLLANO PRO, 1995, CYTOCHROME P 450 STR. Desiraju G. R., 1999, WEAK HYDROGEN BOND. DITCHFIELD R, 1971, J CHEM PHYS, V54, P724, DOI 10.1063/1.1674902. DOLPHOIN D, 1978, PORPHYRIN, V1. EVANS DG, 1988, FARADAY DISCUSS, V86, P55, DOI 10.1039/dc9888600055. Ford TA, 1996, J PHYS CHEM-US, V100, P19336, DOI 10.1021/jp961374a. 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Zahedi M, 1998, THEOCHEM-J MOL STRUC, V452, P125, DOI 10.1016/S0166-1280(98)00141-9. 2001, J PORPHYRINS PHTALLO, V5.}}, doc-delivery-number = {{820VO}}, doi = {{10.1016/j.chemphys.2004.01.024}}, eissn = {{1873-4421}}, interhash = {172679d0a4469bf4f5c9aea97e881982}, intrahash = {5ac7ad6a7d34179151bc3cc551f8df37}, issn = {{0301-0104}}, journal = {{CHEMICAL PHYSICS}}, journal-iso = {{Chem. Phys.}}, keywords = {BF3; ab acceptor complexes} donor initio methods; {porphine;}, keywords-plus = {{DENSITY-FUNCTIONAL THEORY; FREE-BASE PORPHYRIN; AB-INITIO; MESO-TETRAPHENYLPORPHYRINS; MOLECULAR COMPLEXATION; BORON-TRIFLUORIDE; SPECTRUM}}, language = {{English}}, month = {{MAY 31}}, number = {{1}}, number-of-cited-references = {{40}}, orcid-numbers = {{Zahedi, Mansour/0000-0002-2903-9043}}, pages = {{1-7}}, publisher = {{ELSEVIER SCIENCE BV}}, research-areas = {{Chemistry; Physics}}, researcherid-numbers = {{NG, Seik Weng/A-3372-2009 }}, times-cited = {{9}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Prediction of novel complexation of porphine and BF3: Is it a 1 : 1 or 1 : 2 species?}}, type = {{Article}}, unique-id = {{ISI:000221417800001}}, usage-count-last-180-days = {{1}}, usage-count-since-2013 = {{2}}, volume = {{301}}, web-of-science-categories = {{Chemistry, Physical; Physics, Atomic, Molecular \& Chemical}}, year = {{2004}} }