%0 Journal Article %1 ISI:000325124700007 %A Sabounchei, Seyyed Javad %A Panahimehr, Mohammad %A Salehzadeh, Sadegh %A Bayat, Mehdi %A Khavasi, Hamid Reza %A Morales-Morales, David %C 4 PARK SQUARE, MILTON PARK, ABINGDON OX14 4RN, OXON, ENGLAND %D 2013 %I TAYLOR & FRANCIS LTD %J PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS %K NMR X-ray complexes; computational crystal halides mercury(II) multinuclear structure; studies} study; ylide; {Phosphorus %N 12 %P 1743-1758 %R 10.1080/10426507.2013.779274 %T STRUCTURAL, THEORETICAL, AND SPECTROSCOPIC STUDY OF MERCURY(II) COMPLEXES OF TWO NEW UNSYMMETRIC PHOSPHORUS YLIDES %V 188 %X The reaction of Ph2PCH2PPh2 (dppm) with 4-methylphenacyl bromide and 2-(bromoacetyl)naphthalene in chloroform produce the new phosphonium salts Ph2PCH2PPh2CH2C(O)C6H4MeBr (1) and Ph2PCH2PPh2CH2C(O)C10H7Br (2). Further, by reaction of the monophosphonium salts of dppm with the strong base Et3N the corresponding bidentate phosphorus ylides, Ph2PCH2P(Ph)(2) = C(H)C(O)C6H4Me (3) and Ph2PCH2P(Ph)(2) = C(H)C(O)C10H7 (4) were obtained. The reaction of these ligands with mercury(II) halides in dry methanol led to the formation of the mononuclear complexes \HgX2(Ph2PCH2PPh2C(H)C(O)C6H4Me)\ X = Cl (5), Br (6), and I (7) and \HgX2(Ph2PCH2PPh2C(H)C(O)C10H7)\ X = Cl (8), Br (9), and I (10). Characterization of the obtained compounds was performed by elemental analysis, IR, H-1, P-31, and C-13 NMR spectra. The structure of compounds 3 and 10 are unequivocally determined by single crystal X-ray diffraction techniques. X-ray analysis of 10 reveals the presence of mononuclear complex containing Hg atom in a distorted tetrahedral environment. In all complexes, the title ylides are coordinated through the ylidic carbon and the phosphine phosphorus. Computational studies on ligand 4 and complexes 8, 9, and 10 at DFT (B3LYP) level of theory are also reported. It was shown that the formation of P,C-coordinated 1+1 complex 10 is energetically more favored than corresponding P,P-coordinated 1+2 product. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the following free supplemental files: Additional figures

@article{ISI:000325124700007, abstract = {{The reaction of Ph2PCH2PPh2 (dppm) with 4-methylphenacyl bromide and 2-(bromoacetyl)naphthalene in chloroform produce the new phosphonium salts {[}Ph2PCH2PPh2CH2C(O)C6H4Me]Br (1) and {[}Ph2PCH2PPh2CH2C(O)C10H7]Br (2). Further, by reaction of the monophosphonium salts of dppm with the strong base Et3N the corresponding bidentate phosphorus ylides, Ph2PCH2P(Ph)(2) = C(H)C(O)C6H4Me (3) and Ph2PCH2P(Ph)(2) = C(H)C(O)C10H7 (4) were obtained. The reaction of these ligands with mercury(II) halides in dry methanol led to the formation of the mononuclear complexes \{HgX2{[}(Ph2PCH2PPh2C(H)C(O)C6H4Me)]\} {[}X = Cl (5), Br (6), and I (7)] and \{HgX2{[}(Ph2PCH2PPh2C(H)C(O)C10H7)]\} {[}X = Cl (8), Br (9), and I (10)]. Characterization of the obtained compounds was performed by elemental analysis, IR, H-1, P-31, and C-13 NMR spectra. The structure of compounds 3 and 10 are unequivocally determined by single crystal X-ray diffraction techniques. X-ray analysis of 10 reveals the presence of mononuclear complex containing Hg atom in a distorted tetrahedral environment. In all complexes, the title ylides are coordinated through the ylidic carbon and the phosphine phosphorus. Computational studies on ligand 4 and complexes 8, 9, and 10 at DFT (B3LYP) level of theory are also reported. It was shown that the formation of P,C-coordinated 1+1 complex 10 is energetically more favored than corresponding P,P-coordinated 1+2 product. {[}Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the following free supplemental files: Additional figures]}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{4 PARK SQUARE, MILTON PARK, ABINGDON OX14 4RN, OXON, ENGLAND}}, affiliation = {{Sabounchei, SJ (Reprint Author), Univ Bu Ali Sina, Fac Chem, Hamadan 65174, Iran. Sabounchei, Seyyed Javad; Panahimehr, Mohammad; Salehzadeh, Sadegh; Bayat, Mehdi, Univ Bu Ali Sina, Fac Chem, Hamadan 65174, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, GC, Tehran 1983963113, Iran. Morales-Morales, David, Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico.}}, author = {Sabounchei, Seyyed Javad and Panahimehr, Mohammad and Salehzadeh, Sadegh and Bayat, Mehdi and Khavasi, Hamid Reza and Morales-Morales, David}, author-email = {{jsabounchei@yahoo.co.uk}}, biburl = {https://www.bibsonomy.org/bibtex/2418f3f54e072dafe1007dc7a551eedea/hkhavasi}, cited-references = {{AbuGnim C, 1996, J ORGANOMET CHEM, V516, P235, DOI 10.1016/0022-328X(96)06137-2. BARBARO P, 1994, INORG CHEM, V33, P6163, DOI 10.1021/ic00104a029. Bebout DC, 1998, INORG CHEM, V37, P2952, DOI 10.1021/ic971499+. BECKE AD, 1993, J CHEM PHYS, V98, P5648, DOI 10.1063/1.464913. Belluco U, 1998, J ORGANOMET CHEM, V557, P37, DOI 10.1016/S0022-328X(97)00733-X. 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VICENTE J, 1991, J CHEM SOC DALTON, P2579, DOI 10.1039/dt9910002579. Wagner G, 2001, INORG CHEM, V40, P1683, DOI 10.1021/ic000769c. WEGMAN RW, 1987, J CHEM SOC CHEM COMM, P1891, DOI 10.1039/c39870001891. Wittig G., 1980, ANGEW CHEM, V92, P671, DOI 10.1002/ange.19800920904.}}, doc-delivery-number = {{227PB}}, doi = {{10.1080/10426507.2013.779274}}, eissn = {{1563-5325}}, funding-acknowledgement = {{Bu-Ali Sina University}}, funding-text = {{We are grateful to the Bu-Ali Sina University for a grant and Mr. Zebarjadian for recording the NMR spectra. Mehdi Bayat thanks the Marburg University of Germany for their support for doing the computation during his academic visit.}}, interhash = {b922f17328129ad81ef4a5b9983fe8c5}, intrahash = {418f3f54e072dafe1007dc7a551eedea}, issn = {{1042-6507}}, journal = {{PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS}}, journal-iso = {{Phosphorus Sulfur Silicon Relat. Elem.}}, keywords = {NMR X-ray complexes; computational crystal halides mercury(II) multinuclear structure; studies} study; ylide; {Phosphorus}, keywords-plus = {{RAY CRYSTAL-STRUCTURE; PD-II COMPLEXES; PALLADIUM(II) COMPLEXES; SILVER(I) COMPLEXES; MOLECULAR-STRUCTURE; PD(0) COMPLEXES; LIGANDS; COORDINATION; HALIDES; ACTIVATION}}, language = {{English}}, month = {{DEC 1}}, number = {{12}}, number-of-cited-references = {{63}}, orcid-numbers = {{Morales-Morales, David/0000-0002-7984-1819}}, pages = {{1743-1758}}, publisher = {{TAYLOR \& FRANCIS LTD}}, research-areas = {{Chemistry}}, researcherid-numbers = {{Morales-Morales, David/A-1515-2008}}, times-cited = {{4}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{STRUCTURAL, THEORETICAL, AND SPECTROSCOPIC STUDY OF MERCURY(II) COMPLEXES OF TWO NEW UNSYMMETRIC PHOSPHORUS YLIDES}}, type = {{Article}}, unique-id = {{ISI:000325124700007}}, usage-count-last-180-days = {{0}}, usage-count-since-2013 = {{10}}, volume = {{188}}, web-of-science-categories = {{Chemistry, Inorganic \& Nuclear; Chemistry, Organic}}, year = {{2013}} }