Primary phosphines studied by gas-phase electron diffraction and quantum chemical calculations. Are they different from amines?

TY - JOUR

T1 - Primary phosphines studied by gas-phase electron diffraction and quantum chemical calculations. Are they different from amines?

AU - Noble-Eddy, R.

AU - Masters, S.L.

AU - Rankin, D.W.H.

AU - Wann, D.A.

AU - Robertson, H.E.

AU - Khater, B.

AU - Guillemin, J.-C.

N1 - Cited By (since 1996):7 Export Date: 1 October 2013 Source: Scopus CODEN: INOCA doi: 10.1021/ic901018s PubMed ID: 19663455 Language of Original Document: English Correspondence Address: Masters, S. L.; School of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, United Kingdom; email: [email protected] Chemicals/CAS: Amines; Gases; Phosphines References: Brynda, M., (2005) Coord. Chem. Rev., 249, pp. 2013-2034; Groner, P., Johnson, R.D., Durig, J.R.J., (1988) Chem. Phys., 88, pp. 3456-3464; Dinsmore, L.A., Britt, C.O., Boggs, J.E., (1971) J. Chem. Phys., 54, pp. 915-918; Li, Y.S., Cox, A.W., Durig, J.R., (1978) J. Mol. Spectrosc., 70, pp. 34-40; Codding, E.G., Creswell, R.A., Schwendeman, R.H., (1974) Inorg. Chem., 13, pp. 856-859; Wang, I.Y.M., Brott, C.O., Cowley, A.H., Boggs, J.E., (1968) J. Chem. Phys., 48, pp. 812-817; Cervellati, R., Caminati, W., Esposti, C.D., Mirri, A.M., (1977) J. Mol. Spectrosc., 66, pp. 389-398; Demaison, J., Guillemin, J.-C., Mollendal, H., (2001) Inorg. Chem., 40, pp. 3719-3724; Brain, P.T., Rankin, D.W.H., Robertson, H.E., Downs, A.J., Greene, T.M., Hoffman, M., Schleyer, P.V.R., (1995) J. Mol. Struct., 352, pp. 135-144; Mollendal, H., Demiason, J., Guillemin, J.-C., (2002) J. Phys. Chem. A, 106, pp. 11481-11482; Midlendal, H., Demaison, J., Petiprez, D., Wlodarczak, G., Guillemin, J.-C.J., (2005) Phys. Chem. A, 109, pp. 115-121; Drean, P., Leguennec, M., Lopez, J.C., Alonso, J.L., Denis, J.M., Kreglewski, M., Demaison, J., (1994) J. Mol. Spectrosc., 166, pp. 210-223; Cohen, E., McRae, G.A., Goldwhite, H., Stefano, S.D., Beaudet, R.A., (1987) Inorg. Chem., 26, pp. 4000-4003; Naumov, V.A., Tafipol'skii, M.A., Samdal, S., (2003) Russ. J. Gen. Chem., 73, pp. 896-902; Noble-Eddy, R., Masters, S.L., Rankin, D.W.H., Wann, D.A., Khater, B., Guillemin, J.-C., (2008) Dalton Trans., pp. 5041-5047; Mastryukov, V.S., Boggs, J.E., Durig, J.R., (2001) J. Mol. Struct., 567-568, pp. 101-106; Serre, S.L., Guillemin, J.-C., Kárpáti, T., Soos, L., Nyulászi, L., Veszprémi, T., (1998) J. Org. Chem., 63, pp. 59-68; Guillemin, J.-C., Malagu, K., (1999) Organometallics, 18, pp. 5259-5263; Guillemin, J.-C., Savignac, P., Denis, J.-M., (1991) Inorg. Chem., 30, pp. 2170-2173; Cabioch, J.-L., Denis, J.-M., (1989) J. Organomet. Chem., 377, pp. 227-233; Horner, L., Hoffmann, H., Beck, P., (1958) Chem. Ber., 91, pp. 1583-1588; Cabioch, J.-L., Pellerin, B., Denis, J.-M., (1989) Phosphorus, Sulfur Silicon Relat. Elem., 44, pp. 27-32; Margules, L., Demaison, J., Sreeja, P.B., Guillemin, J.-C.J., (2006) Mol. Spectrosc, 238, pp. 234-240; Albrand, J.P., Anderson, S.P., Goldwhite, H., Huff, L., (1975) Inorg. Chem., 14, pp. 570-573; http://www.nsccs.ac.uk, EPSRC National Service for Computational Chemistry Softwarehttp://www.eastchem.ac.uk/rcf), EaStCHEM Research Computing Facilityhttp://www.edi.kt.org, This facility is partially supported by the eDIKT initiativeFrisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery Jr., J.A., Pople, J.A., (2004) Gaussian 03, Revision C.02, , Gaussian, Inc. ; Wallingford, CT; Binkley, J.S., Pople, J.A., Hehre, W.J., (1980) J. Am. Chem. Soc., 102, pp. 939-947; Gordon, M.S., Binkley, J.S., Pople, J.A., Pietro, W.J., Hehre, W.J., (1982) J. Am. Chem. Soc., 104, pp. 2797-2803; Pietro, W.J., Francl, M.M., Hehre, W.J., Defrees, D.J., Pople, J.A., Binkley, J.S., (1982) J. Am. Chem. Soc., 104, pp. 5039-5048; Roothaan, C.C.J., (1951) Rev. Mod. Phys., 23, pp. 69-89; Mpller, C., Plesset, M.S., (1934) Phys. Rev., 46, pp. 618-622; Hehre, W.J., Ditchfield, R., Pople, J.A., (1972) J. Chem. Phys., 56, pp. 2257-2261; Hariharan, P.C., Pople, J.A., (1973) Theor. Chim. Acta, 28, pp. 213-222; Gordon, M.S., (1980) Chem. Phys. Lett., 76, pp. 163-168; McLean, A.D., Chandler, G.S., (1980) J. Chem. Phys., 72, pp. 5639-5648; Krishnan, R., Binkley, J.S., Seeger, R., Pople, J.A., (1980) J. Chem. Phys., 72, pp. 650-654; Woon, D.E., Dunning Jr., T.H., (1993) J. Chem. Phys., 98, pp. 1358-1371; Kendall, R.A., Dunning Jr., T.H., Harrison, R.J., (1992) J. Chem. Phys., 96, pp. 6796-6806; Dunning Jr., T.H., (1989) J. Chem. Phys., 90, pp. 1007-1023; Peterson, K.A., Woon, D.E., Dunning Jr., T.H., (1994) J. Chem. Phys., 100, pp. 7410-7415; Wilson, A., Dunning Jr., T.H., (1996) J. Mol. Struct., THEOCHEM, 388, pp. 339-349; Frisch, M.J., Head-Gordon, M., Pople, J.A., (1990) Chem. Phys. Lett., 166, pp. 275-280; Frisch, M.J., Head-Gordon, M., Pople, J.A., (1990) Chem. Phys. Lett., 166, pp. 281-290; Sipachev, V.A., (1985) J. Mol. Struct., THEOCHEM, 121, pp. 143-151; Huntley, C.M., Laurenson, G.S., Rankin, D.W.H., (1980) J. Chem. Soc. Dalton Trans., pp. 954-957; Fleischer, H., Wann, D.A., Hinchley, S.L., Borisenko, K.B., Lewis, J.R., Mawhorter, R.J., Robertson, H.E., Rankin, D.W.H., (2005) Dalton. Trans., pp. 3221-3228; Hinchley, S.L., Robertson, H.E., Borisenko, K.B., Turner, A.R., Johnston, B.F., Rankin, D.W.H., Ahmadian, M., Cowley, A.H., (2004) Dalton Trans., pp. 2469-2476; Ross, A.W., Fink, M., Hilderbrandt, R., (1992) International Tables for Crystallography, C, p. 245. , Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Dordrecht, Netherlands; Blake, A.J., Brain, P.T., McNab, H., Miller, J., Morrison, C.A., Parsons, S., Rankin, D.W.H., Smart, B.A., (1996) J. Phys. Chem., 100, pp. 12280-12287; Brain, P.T., Morrison, C.A., Parsons, S., Rankin, D.W.H., (1996) J. Chem. Soc. Dalton Trans., pp. 4589-4596; Mitzel, N.W., Rankin, D.W.H., (2003) Dalton Trans., pp. 3650-3662; Roussy, G., Demaison, J., Barriol, J., Rudolph, H.D., (1971) J. Mol. Spectrosc., 38, pp. 535-544; Botskor, I., Rudolph, H.D., Roussy, G.J., (1974) J. Mol. Spectrosc., 52, pp. 457-484; Botskor, I., Rudolph, H.D., Roussy, G.J., (1974) J. Mol. Spectrosc., 53, pp. 15-36; Botskor, I., Rudolph, H.D., (1978) J. Mol. Spectrosc., 71, pp. 430-435; Hakiki, A., Ripoll, J.-L., Thuillier, A., (1984) Tetrahedron Lett., 25, pp. 3459-3460; Hamada, Y., Hashiguchi, K., Tsuboi, M., Koga, Y., Kondo, S., (1984) J. Mol. Spectrosc., 105, pp. 93-104; Hamada, Y., Sato, N., Tsuboi, M., (1987) J. Mol. Spectrosc., 124, pp. 172-178; McNaughton, D., Robertson, E.G., (1994) J. Mol, Spectrosc., 163, pp. 80-85; Melandri, S., Maris, A., Favero, P.G., Caminati, W., (2001) Chem. Phys. Chem., 2, pp. 172-177; Bohme, H., Viehe, H.G., (1979) Iminium Salts in Organic Chemistry, , John Wiley & Sons: New York-London; Lee, P.L., Cohn, K., Schwendeman, R.H., (1972) Inorg. Chem., 11, pp. 1917-1920; Wentrup, C., Briehl, H., Lorencak, P., Vogelbacher, U.J., Winter, H.W., Maquestiau, A., Flammang, R., (1988) J. Am. Chem. Soc., 110, pp. 1337-1343; Schultz, G., Portalone, G., Romando, F., Domenicano, A., Hargittai, I., (1996) Struct. Chem., 7, pp. 59-71; Chou, K.-T., Zhou, G.-D., Chen, W., (1993) Fundamentals of Structural Chemistry, , World Scientific: River Edge, NJ

PY - 2009/9/7

Y1 - 2009/9/7

N2 - The molecular structures of allyl-, allenyl-, propargyl-, vinyl-, ethynyl-, phenyl-, benzyl-, and chloromethyl- phosphine have been determined from gas-phase electron diffraction data employing the SARACEN method. The experimental geometric parameters are compared with those obtained using ab initio calculations performed at the MP2 level using both Pople-type basis sets and the correlation-consistent basis sets of Dunning. The structure and conformational behavior of each molecule have been analyzed and, where possible, comparisons made to the analogous amine. For systems with multiple conformers, differences in the CCP bond angle of ∼5° between conformers are common. Trends in the key parameters are identified and compared with those found in similar systems. © 2009 American Chemical Society.

AB - The molecular structures of allyl-, allenyl-, propargyl-, vinyl-, ethynyl-, phenyl-, benzyl-, and chloromethyl- phosphine have been determined from gas-phase electron diffraction data employing the SARACEN method. The experimental geometric parameters are compared with those obtained using ab initio calculations performed at the MP2 level using both Pople-type basis sets and the correlation-consistent basis sets of Dunning. The structure and conformational behavior of each molecule have been analyzed and, where possible, comparisons made to the analogous amine. For systems with multiple conformers, differences in the CCP bond angle of ∼5° between conformers are common. Trends in the key parameters are identified and compared with those found in similar systems. © 2009 American Chemical Society.

KW - amine

KW - phosphine derivative

KW - article

KW - chemical model

KW - chemical structure

KW - chemistry

KW - computer simulation

KW - electron

KW - gas

KW - quantum theory

KW - synthesis

KW - Amines

KW - Computer Simulation

KW - Electrons

KW - Gases

KW - Models, Chemical

KW - Models, Molecular

KW - Molecular Structure

KW - Phosphines

KW - Quantum Theory

U2 - 10.1021/ic901018s

DO - 10.1021/ic901018s

M3 - Article

SN - 0020-1669

VL - 48

SP - 8603

EP - 8612

JO - Inorganic Chemistry

JF - Inorganic Chemistry

IS - 17

ER -