The Lewis acidities of gold(I) and gold(III) derivatives: a theoretical study of complexes of AuCl and AuCl3

Structural Chemistry - Tập 31 - Trang 1909-1918 - 2020
Cristina Trujillo1, Goar Sánchez-Sanz2, José Elguero3, Ibon Alkorta3
1School of Chemistry, Trinity Biomedical Sciences Institute, Trinity College Dublin, Dublin 2, Ireland
2Irish Centre of High-End Computing, Grand Canal Quay, Dublin 2, Ireland & School of Chemistry, University College Dublin, Dublin 4, Ireland
3Instituto de Química Médica, CSIC, Madrid, Spain

Tóm tắt

Chloride complexes of gold(I) (seventeen) and gold(III) (seventeen) with different ligands (including H, C, N, O, P, S as interacting atoms) have been studied at the CCSD(T)/CBS level. The computed geometries were compared with those found in the Cambridge Structural Database and the dissociation energies related with those previously reported in the literature by Yamamoto et al. Some special processes catalysed by these gold complexes such as bond-breaking (dihydrogen, cyclopropane) and arenes reactivity were studied in detail.

Tài liệu tham khảo

Dhar S, Daniel WL, Giljohann DA, Mirkin CA, Lippard SJ (2009). J Am Chem Soc 131:14652–14653 Dada O, Sánchez-Sanz G, Tacke M, Zhu X (2018). Tetrahedron Lett 59:2904–2908 Curran D, Dada O, Müller-Bunz H, Rothemund M, Sánchez-Sanz G, Schobert R, Zhu X, Tacke M (2018). Molecules 23:2031 Wolfgang W, Oyinlola D, Cillian OB, Ingo O, Goar S-S, Claudia S, Carsta W, Xiangming Z, Matthias T (2017). Lett Drug Des Discov 14:125–134 Fernández-Gallardo J, Elie BT, Sulzmaier FJ, Sanaú M, Ramos JW, Contel M (2014). Organometallics 33:6669–6681 Son G, Son Y, Jeon H, Kim J-Y, Lee S (2020). Scripta Mater 174:33–38 Calzolari A, Cicero G, Cavazzoni C, Di Felice R, Catellani A, Corni S (2010). J Am Chem Soc 132:4790–4795 Iori F, Di Felice R, Molinari E, Corni S (2009). J Comput Chem 30:1465–1476 Shen HC (2008). Tetrahedron 64:3885–3903 Fürstner A (2009). Chem Soc Rev 38:3208–3221 Schmidbaur H, Schier A (2010). Organometallics 29:2–23 Schmidbaur H, Schier A (2012). Arab J Sci Eng 37:1187–1225 Shen HC, Graham TH (2013). Drug Discov Today Technol 10:e3–e14 Boronat M, Leyva-Pérez A, Corma A (2014). Acc Chem Res 47:834–844 Soriano E, Fernández I (2014). Chem Soc Rev 43:3041–3105 Wang Y, Muratore ME, Echavarren AM (2015). Chem Eur J 21:7332–7339 Dorel R, Echavarren AM (2015). Chem Rev 115:9028–9072 Ranieri B, Escofet I, Echavarren AM (2015). Org Biomol Chem 13:7103–7118 Legon AC, Walker NR (2018). PCCP 20:19332–19338 Vogel P, Houk KN (2019) Organic chemistry. Theory, reactivity and mechanisms in modern synthesis. Wiley-VCH Verlag GmbH, Weinheim Hashmi ASK, Toste DF (2012) Modern gold catalyzed synthesis. Wiley-VCH Verlag GmbH, Weinheim Pombeiro AJL (2013) Advances in organometallic chemistry and catalysis: the silver/gold Jubilee International conference on organometallic chemistry celebratory book. Wiley & sons Inc, Hoboken Pyykkö P (2008). Chem Soc Rev 37:1967–1997 Söhnel T, Hermann H, Schwerdtfeger P (2005). J Phys Chem B 109:526–531 Persson K (2014) Halder A, Kundu P, Ravishankar N, Ramanath G (2009). J Phys Chem C 113:5349–5351 Clark ES, Templeton DH, MacGillavry CH (1958). Acta Crystallogr 11:284–288 Hargittai M, Schulz A, Réffy B, Kolonits M (2001). J Am Chem Soc 123:1449–1458 Evans CJ, Gerry MCL (2000). J Mol Spectrosc 203:105–117 Allen FH (2002). Acta Crystallogr Sect B: Struct Sci 58:380–388 Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, van de Streek J (2006). J Appl Crystallogr 39:453–457 Hellenbrandt M (2004). Crystallogr Rev 10:17–22 Obenchain DA, Frank DS, Grubbs GS, Pickett HM, Novick SE (2017). J Chem Phys 146:204302 Evans CJ, Reynard LM, Gerry MCL (2001). Inorg Chem 40:6123–6131 Mullaney JC, Stephens SL, Zaleski DP, Sprawling MJ, Tew DP, Walker NR, Legon AC (2015). J Phys Chem A 119:9636–9643 Medcraft C, Bittner DM, Tew DP, Walker NR, Legon AC (2016). J Chem Phys 145:194306 Patil NT, Yamamoto Y (2007) Arkivoc v:6-19 Yamamoto Y (2007). J Org Chem 72:7817–7831 Yamamoto Y, Gridnev ID, Patil NT, Jin T (2009). Chem Commun:5075–5087 Gorin DJ, Toste FD (2007). Nature 446:395–403 Gaillard S, Slawin AMZ, Bonura AT, Stevens ED, Nolan SP (2010). Organometallics 29:394–402 Shaw AP, Ghosh MK, Törnroos KW, Wragg DS, Tilset M, Swang O, Heyn RH, Jakobsen S (2012). Organometallics 31:7093–7100 Zhu R-X, Zhang D-J, Guo J-X, Mu J-L, Duan C-G, Liu C-B (2010). J Phys Chem A 114:4689–4696 Rabaâ H, Engels B, Hupp T, Hashmi ASK (2007). Int J Quantum Chem 107:359–365 Esterhuysen C, Frenking G (2011). Chem Eur J 17:9944–9956 Li H, Li Q, Li R, Li W, Cheng J (2011). J Chem Phys 135:074304 Grabowski SJ, Ruipérez F (2016). Phys Chem Chem Phys 18:12810–12818 Pérez-Bitrián A, Baya M, Casas JM, Falvello LR, Martín A, Menjón B (2017). Chem Eur J 23:14918–14930 Zhang G, Yue H, Weinhold F, Wang H, Li H, Chen D (2015). ChemPhysChem 16:2424–2431 Møller C, Plesset MS (1934). Phys Rev 46:618–622 Dunning TH (1989). J Chem Phys 90:1007–1023 Papajak E, Zheng J, Xu X, Leverentz HR, Truhlar DG (2011). J Chem Theor Comput 7:3027–3034 Peterson KA, Puzzarini C (2005). Theor Chem Acc 114:283–296 Purvis GD, Bartlett RJ (1982). J Chem Phys 76:1910–1918 Halkier A, Klopper W, Helgaker T, Jørgensen P, Taylor PR (1999). J Chem Phys 111:9157–9167 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2016) Todd A. Keith Gaussian 16, revision B.01. Gaussian, Inc., Wallingford Lu T, Chen F (2012). J Comput Chem 33:580–592 Jmol: an open-source Java viewer for chemical structures in 3D. http://www.jmol.org/ Rocchigiani L, Budzelaar PHM, Bochmann M (2019). Chem Sci 10:2633–2642 Groom CR, Bruno IJ, Lightfoot MP, Ward SC (2016). Acta Crystallogr Sect B 72:171–179 Dinger MB, Henderson W (1999). J Organomet Chem 577:219–222 Jiménez-Núñez E, Echavarren AM (2008). Chem Rev 108:3326–3350 Jiang M, Liu L-P, Shi M, Li Y (2010). Org Lett 12:116–119 Huang H, Zhou Y, Liu H (2011). Beilstein J Org Chem 7:897–936 Zang W, Wei Y, Shi M (2019). Chem Commun 55:8126–8129 Bauzá A, Frontera A (2018). Inorganics 6:64 Frontera A, Bauzá A (2018). Chem Eur J 24:7228–7234 Fuchita Y, Utsunomiya Y, Yasutake M (2001) J Chem Soc. Dalton Trans:2330–2334 de Haro T, Nevado C (2001). J Am Chem Soc 132:1512–1513 de Haro T, Nevado C (2011). Synthesis 2011:2530–2539 Gaillard S, Slawin AMZ, Nolan SP (2010). Chem Commun 46:2742–2744 Lu P, Boorman TC, Slawin AMZ, Larrosa I (2010). J Am Chem Soc 132:5580–5581 Mascal M, Armstrong A, Bartberger MD (2002). J Am Chem Soc 124:6274–6276 Quiñonero D, Garau C, Rotger C, Frontera A, Ballester P, Costa A, Deyà PM (2002). Angew Chem Int Ed 41:3389–3392 Alkorta I, Rozas I, Elguero J (2002). J Am Chem Soc 124:8593–8598 Salai Cheettu Ammal S, Ananthavel SP, Venuvanalingam P, Hegde MS (1998). J Phys Chem A 102:532–536 Wei Y, Wang B-W, Hu S-W, Chu T-W, Tang L-T, Liu X-Q, Wang Y, Wang X-Y (2005). J Phys Org Chem 18:625–631