Abstract
This review concentrates on the results obtained thus far in
cross-coupling reactions utilising Pd-PEPPSI-IPr
(pre)catalyst. Results from computational studies expose possible
factors behind the high reactivity of this complex, as well as mechanistic
details for the IPr-Pd-mediated alkyl-alkyl Negishi
cross-coupling.
1 Introduction
2 Evolution to Pd-PEPPSI Complexes
2.1 Background of NHCs; Unraveling Electronic and Steric Components
2.2 Design and Preparation of Pd-PEPPSI Complexes
2.3 Mechanism of Activation and Role in the Catalytic Cycle
3 Cross-Coupling Results with Pd-PEPPSI Complexes
3.1 General Cross-Coupling Scheme
3.2 The Suzuki-Miyaura Reaction
3.3 The Kumada-Tamao-Corriu Reaction
3.4 The Negishi Reaction
3.5 Buchwald-Hartwig-Yagupol’skii
Amination
4 Theory and Computation
4.1 Theory
4.2 Computation
4.3 Geometric Structure
4.4 Reaction Profile
4.5 Interactions
4.6 Atoms-in-Molecules
5 Conclusions
Key words
palladium - cross-coupling - PEPPSI - computation
References
<A NAME="RC03808SS-1">1 </A>
Herrmann WA.
Angew.
Chem. Int. Ed.
2002,
41:
1290
<A NAME="RC03808SS-2">2 </A>
Kantchev EAB.
O’Brien CJ.
Organ MG.
Angew. Chem. Int. Ed.
2007,
46:
2768
<A NAME="RC03808SS-3">3 </A>
Kantchev EAB.
O’Brien CJ.
Organ MG.
Aldrichimica Acta
2006,
39:
97
<A NAME="RC03808SS-4">4 </A>
Herrmann WA.
Öfele K.
Preysing D.-v.
Schneider SK.
J. Organomet. Chem.
2003,
687:
229
<A NAME="RC03808SS-5">5 </A>
O’Brien CJ.
Kantchev EAB.
Valente C.
Hadei N.
Chass GA.
Lough A.
Hopkinson AC.
Organ MG.
Chem. Eur. J.
2006,
12:
4743
<A NAME="RC03808SS-6">6 </A>
Valente C.
Baglione S.
Candito D.
O’Brien CJ.
Organ MG.
Chem. Commun.
2008,
735
<A NAME="RC03808SS-7">7 </A>
Organ MG.
Avola S.
Dubovyk I.
Hadei N.
Kantchev EAB.
O’Brien CJ.
Valente C.
Chem. Eur. J.
2006,
12:
4749
<A NAME="RC03808SS-8">8 </A>
Organ MG.
Abdel-Hadi M.
Avola S.
Hadei N.
Nasielski J.
O’Brien CJ.
Valente C.
Chem. Eur. J.
2007,
13:
150
<A NAME="RC03808SS-9">9 </A>
Organ MG.
Abdel-Hadi M.
Avola S.
Dubovyk I.
Hadei N.
Kantchev EAB.
O’Brien CJ.
Valente C.
Chem.
Eur. J.
2008,
14:
2443
<A NAME="RC03808SS-10">10 </A>
Wanzlick H.-W.
Schönherr H.-J.
Angew. Chem.,
Int. Ed. Engl.
1968,
7:
141
<A NAME="RC03808SS-11">11 </A>
Öfele K.
J.
Organomet. Chem.
1968,
12:
P42
<A NAME="RC03808SS-12">12 </A>
Arduengo AJ.
Harlow RL.
Kline M.
J. Am. Chem. Soc.
1991,
113:
361
<A NAME="RC03808SS-13">13 </A>
Nair V.
Bindu S.
Sreekumar V.
Angew.
Chem. Int. Ed.
2004,
43:
5130
<A NAME="RC03808SS-14">14 </A>
Perry MC.
Burgess K.
Tetrahedron: Asymmetry
2003,
14:
951
<A NAME="RC03808SS-15">15 </A>
Crudden CM.
Allen DP.
Coord. Chem. Rev.
2004,
248:
2247
<A NAME="RC03808SS-16">16 </A>
Nolan SP.
Scott NM.
Eur. J. Inorg. Chem.
2005,
1815
<A NAME="RC03808SS-17">17 </A>
Crabtree RH.
J.
Organomet. Chem.
2005,
690:
5451
<A NAME="RC03808SS-18">18 </A>
Youngs WJ.
Garrison JC.
Chem. Rev.
2005,
105:
3978
<A NAME="RC03808SS-19">19 </A>
Cavallo L.
Correa A.
Costabile C.
Jacobsen H.
J. Organomet. Chem.
2005,
690:
5407
<A NAME="RC03808SS-20">20 </A>
Herrmann WA.
Fischer EJ.
Köchter C.
Arthus GRJ.
Angew.
Chem., Int. Ed. Engl.
1995,
107:
2602
<A NAME="RC03808SS-21">21 </A>
Herrmann WA.
Mihalios D.
Öfele K.
Kiprof P.
Belmedjahed F.
Chem.
Ber.
1992,
125:
1795
<A NAME="RC03808SS-22">22 </A>
Öfele K.
Herrmann WA.
Mihalios D.
Elison M.
Herdtweck E.
Scherer W.
Mink J.
J.
Organomet. Chem.
1993,
459:
177
<A NAME="RC03808SS-23">23 </A>
Herrmann WA.
Öfele K.
Elison M.
Kuhn FE.
Roesky PW.
J.
Organomet. Chem.
1994,
480:
C7
<A NAME="RC03808SS-24">24 </A>
Littke AF.
Fu GC.
Angew. Chem. Int. Ed.
2002,
41:
4176
<A NAME="RC03808SS-25">25 </A>
Cárdenas DJ.
Angew. Chem. Int. Ed.
1999,
38:
3018
<A NAME="RC03808SS-26">26 </A>
Netherton MR.
Fu GC.
Adv. Synth. Catal.
2004,
346:
1525
<A NAME="RC03808SS-27">27 </A>
Frisch AC.
Beller M.
Angew. Chem. Int. Ed.
2005,
44:
674
<A NAME="RC03808SS-28">28 </A>
Valentine DHJ.
Hillhouse JH.
Synthesis
2003,
2437
<A NAME="RC03808SS-29">29 </A>
Dias PB.
Piedade MEM.
Simões JAM.
Coord. Chem. Rev.
1994,
135-136:
737
<A NAME="RC03808SS-30">30 </A>
Tolman CA.
Chem.
Rev.
1977,
77:
313
<A NAME="RC03808SS-31">31 </A>
Mauger CC.
Mignani GA.
Aldrichimica Acta
2006,
39:
17
<A NAME="RC03808SS-32">32 </A>
Amyes TL.
Diver ST.
Richard JP.
Rivas FM.
Toth K.
J. Am. Chem. Soc.
2004,
126:
4366
<A NAME="RC03808SS-33">33 </A>
Frohlich N.
Pindun U.
Stahl M.
Frenking G.
Organometallics
1997,
16:
442
<A NAME="RC03808SS-34">34 </A>
Chen H.
Justes DR.
Cooks RG.
Org. Lett.
2005,
7:
3949
<A NAME="RC03808SS-35">35 </A>
Cowley AH.
J.
Organomet. Chem.
2001,
617-618:
105
<A NAME="RC03808SS-36">36 </A>
Chianese AR.
Li X.
Janzen MC.
Faller JW.
Crabtree RH.
Organometallics
2003,
22:
1663
<A NAME="RC03808SS-37">37 </A>
Dorta R.
Stevens ED.
Scott NM.
Costabile C.
Cavallo L.
Hoff CD.
Nolan SP.
J. Am. Chem. Soc.
2004,
127:
2485
<A NAME="RC03808SS-38">38 </A>
Herrmann WA.
Schütz J.
Frey GD.
Herdtweck E.
Organometallics
2006,
25:
2437
<A NAME="RC03808SS-39">39 </A>
O’Brien CJ.
Kantchev EAB.
Chass GA.
Hadei N.
Hopkinson AC.
Organ MG.
Setiadi DH.
Tang T.-H.
Fang D.-C.
Tetrahedron
2005,
61:
9723
<A NAME="RC03808SS-40">40 </A>
Culkin DA.
Hartwig JF.
Organometallics
2004,
23:
3398
<A NAME="RC03808SS-41">41 </A>
Mann G.
Shelby Q.
Roy AH.
Hartwig JF.
Organometallics
2003,
22:
2775
<A NAME="RC03808SS-42">42 </A>
Page PCB.
Buckley BR.
Christie SDR.
Edgar M.
Poulton AM.
Elsegood MRJ.
McKee VJ.
J. Organomet.
Chem.
2005,
690:
6210
<A NAME="RC03808SS-43">43 </A>
Lebel H.
Janes MK.
Charette AB.
Nolan SP.
J.
Am. Chem. Soc.
2004,
126:
5046
<A NAME="RC03808SS-44">44 </A>
Ma Y.
Song C.
Jiang W.
Xue G.
Cannon JF.
Wang X.
Andrus MB.
Org. Lett.
2003,
5:
4635
<A NAME="RC03808SS-45">45 </A>
Love JA.
Morgan JP.
Trnka TM.
Grubbs RG.
Angew.
Chem. Int. Ed.
2002,
41:
4035
<A NAME="RC03808SS-46">46 </A>
Hall DG.
Boronic
Acids: Preparation Applications in Organic Synthesis and Medicine
Wiley-VCH;
Weinheim:
2005.
<A NAME="RC03808SS-47">47 </A>
Thomas SE.
Organic synthesis: the roles of boron and silicon
Oxford
University Press;
Oxford:
1991.
<A NAME="RC03808SS-48">48 </A>
de Meijere A.
Diederich F.
Metal-catalyzed
cross-coupling reactions
2nd ed.:
Miyarua N.
Wiley-VCH;
Weinheim:
2004.
p.41-123
<A NAME="RC03808SS-49">49 </A>
Chemler SR.
Trauner D.
Danishefsky SJ.
Angew. Chem.
Int. Ed.
2001,
40:
4544
<A NAME="RC03808SS-50">50 </A>
Negishi E.-i.
Aspects of Mechanism and Organometallic Chemistry
Brewster JH.
Plenum;
New
York:
1978.
p.285
<A NAME="RC03808SS-51">51 </A>
Negishi E.-i.
J.
Organomet. Chem.
2002,
653:
34
<A NAME="RC03808SS-52">52 </A>
Miyaura N.
Yamada K.
Suzuki A.
Tetrahedron
Lett.
1979,
20:
3437
<A NAME="RC03808SS-53">53 </A>
Miyarua N.
Suzuki A.
J. Chem. Soc. Chem. Commun.
1979,
866
<A NAME="RC03808SS-54">54 </A>
Bellina F.
Carpita A.
Rossie R.
Synthesis
2004,
2419
<A NAME="RC03808SS-55">55 </A>
Miura M.
Angew.
Chem. Int. Ed.
2004,
43:
2201
<A NAME="RC03808SS-56">56 </A>
Miyaura N.
Top.
Curr. Chem.
2002,
219:
11
<A NAME="RC03808SS-57">57 </A>
Suzuki A.
J.
Organomet. Chem.
1999,
576:
147
<A NAME="RC03808SS-58">58 </A>
Miyaura N.
Suzuki A.
Chem. Rev.
1995,
95:
2457
<A NAME="RC03808SS-59">59 </A>
Herrmann WA.
Reisinger C.-P.
Spiegler M.
J. Organomet.
Chem.
1998,
557:
93
<A NAME="RC03808SS-60">60 </A>
Zhang C.
Huang J.
Trudell ML.
Nolan SP.
J. Org. Chem.
1999,
64:
3804
<A NAME="RC03808SS-61">61 </A>
Andrus MB.
Song C.
Org. Lett.
2001,
3:
3761
<A NAME="RC03808SS-62">62 </A>
Gstöttmayr CWK.
Böhm VPW.
Herdtweck E.
Grosche M.
Herrmann WA.
Angew.
Chem. Int. Ed.
2002,
41:
1363
<A NAME="RC03808SS-63">63 </A>
Altenhoff G.
Goddard R.
Lehmann CW.
Glorius F.
Angew. Chem. Int. Ed.
2003,
42:
3690
<A NAME="RC03808SS-64">64 </A>
Navarro O.
Kelly RA.
Nolan SP.
J.
Am. Chem. Soc.
2003,
125:
16194
<A NAME="RC03808SS-65">65 </A>
Song C.
Ma Y.
Chai Q.
Ma C.
Jiang W.
Andrus MB.
Tetrahedron
2005,
61:
7438
<A NAME="RC03808SS-66">66 </A>
Altenhoff G.
Goddard R.
Lehmann CW.
Glorius F.
J. Am. Chem. Soc.
2004,
126:
15195
<A NAME="RC03808SS-67">67 </A>
Navarro O.
Kaur H.
Mahjoor P.
Nolan SP.
J. Org. Chem.
2004,
69:
3173
<A NAME="RC03808SS-68">68 </A>
Cesar V.
Bellemin-Laponnaz S.
Gade LH.
Organometallics
2002,
21:
5204
<A NAME="RC03808SS-69">69 </A>
Palencia H.
Garcia-Jimenez F.
Takacs JM.
Tetrahedron Lett.
2004,
45:
3849
<A NAME="RC03808SS-70">70 </A>
Schneider SK.
Herrmann WA.
Herdtweck E.
J.
Mol. Catal.
2006,
245:
248
<A NAME="RC03808SS-71">71 </A>
Fuller AA.
Hester HR.
Salo EV.
Stevens EP.
Tetrahedron Lett.
2003,
44:
2935
<A NAME="RC03808SS-72">72 </A>
Abraham MH.
Grellier PL.
The
Chemistry of the Metal-Carbon Bond
Hartley FR.
Patai S.
Wiley;
New York:
1985.
p.25
<A NAME="RC03808SS-73">73 </A>
McDougal NT.
Schaus SE.
J. Am. Chem. Soc.
2003,
125:
12094
<A NAME="RC03808SS-74">74 </A>
McDougal NT.
Trevellini WL.
Rodgen SA.
Kliman LT.
Schaus SE.
Adv. Synth. Catal.
2004,
346:
1231
<A NAME="RC03808SS-75">75 </A>
Perkins JR.
Carter RG.
J. Am. Chem. Soc.
2008,
130:
3290
<A NAME="RC03808SS-76">76 </A>
Littke AF.
Dai C.
Fu GC.
J.
Am. Chem. Soc.
2000,
122:
4020
<A NAME="RC03808SS-77">77 </A>
Barder TE.
Walker SD.
Martinelli JR.
Buchwald SL.
J.
Am. Chem. Soc.
2005,
127:
4749
<A NAME="RC03808SS-78">78 </A>
Arentsen K.
Caddick S.
Cloke FGN.
Herring AP.
Hitchcock PB.
Tetrahedron Lett.
2004,
45:
3511
<A NAME="RC03808SS-79">79 </A>
Singh R.
Viciu MS.
Kramareva N.
Navarro O.
Nolan SP.
Org.
Lett.
2005,
7:
1829
<A NAME="RC03808SS-80">80 </A>
Tamao K.
Sumitani K.
Kumada M.
J.
Am. Chem. Soc.
1972,
94:
4374
<A NAME="RC03808SS-81">81 </A>
Corriu RJP.
Masse JP.
Chem.
Commun.
1972,
144
<A NAME="RC03808SS-82">82 </A>
Yamamura M.
Moritani I.
Murahashi S.
J.
Organomet. Chem.
1975,
61:
C39
<A NAME="RC03808SS-83">83 </A>
Huang J.
Nolan SP.
J. Am. Chem. Soc.
1999,
121:
9889
<A NAME="RC03808SS-84">84 </A>
Frisch AC.
Rataboul F.
Zapf A.
Beller M.
J. Organomet. Chem.
2003,
687:
403
<A NAME="RC03808SS-85">85 </A>
Frisch AC.
Zapf A.
Briel O.
Kayser B.
Shaikh N.
Beller M.
J. Mol. Catal.
2004,
214:
231
<A NAME="RC03808SS-86">86 </A>
Negishi E.-i.
King AO.
Okukado N.
J.
Org. Chem.
1977,
42:
1821
<A NAME="RC03808SS-87">87 </A>
King AO.
Okukado N.
Negishi E.-i.
Chem.
Commun.
1977,
683
<A NAME="RC03808SS-88">88 </A>
Knochel P.
Jones P.
Organozinc
Reagents - A Practical Approach
Oxford
University Press;
Oxford:
1999.
<A NAME="RC03808SS-89">89 </A>
Iyer S.
Jayanthi A.
Synlett
2003,
1125
<A NAME="RC03808SS-90">90 </A>
Zhou J.
Fu GC.
J. Am. Chem. Soc.
2003,
125:
12527
<A NAME="RC03808SS-91">91 </A>
Zhu L.
Wehmeyer RM.
Rieke RD.
J.
Org. Chem.
1991,
56:
1445
<A NAME="RC03808SS-92">92 </A>
Rieke RD.
Hanson MV.
Brown JD.
Niu QJ.
J.
Org. Chem.
1996,
61:
2726
<A NAME="RC03808SS-93">93 </A>
Hadei N.
Kantchev EAB.
O’Brien CJ.
Organ MG.
Org.
Lett.
2005,
7:
3805
<A NAME="RC03808SS-94">94 </A>
Hou S.
Org.
Lett.
2003,
5:
423
<A NAME="RC03808SS-95">95 </A>
Kosugi M.
Kameyama M.
Migita T.
Chem.
Lett.
1983,
927
<A NAME="RC03808SS-96">96 </A>
Boger DL.
Panek JS.
Tetrahedron Lett.
1984,
25:
3175
<A NAME="RC03808SS-97">97 </A>
Kondratenko NV.
Kolomeitsev AA.
Mogilevskaya VO.
Varlamova NM.
Yagupol’skii LM.
J.
Org. Chem. USSR (Engl. Transl.)
1986,
22:
1547 ; translated from Zh. Org.
Khim . 1986 , 22 ,
1721 (original article submitted March 26, 1985)
<A NAME="RC03808SS-98">98 </A>
Guram AS.
Rennels RA.
Buchwald SL.
Angew. Chem. Int. Ed.
1995,
34:
1348
<A NAME="RC03808SS-99">99 </A>
Louie J.
Hartwig JF.
Tetrahedron Lett.
1995,
36:
3609
<A NAME="RC03808SS-100">100 </A>
Schlummer B.
Scholz U.
Adv. Synth. Catal.
2004,
346:
1599
<A NAME="RC03808SS-101">101 </A>
Muci AR.
Buchwald SL.
Top. Curr. Chem.
2002,
219:
131
<A NAME="RC03808SS-102">102 </A>
Huang J.
Grasa GA.
Nolan SP.
Org.
Lett.
1999,
1:
1307
<A NAME="RC03808SS-103">103 </A>
Grasa GA.
Viciu MS.
Huang J.
Nolan SP.
J. Org. Chem.
2001,
66:
7729
<A NAME="RC03808SS-104">104 </A>
Viciu MS.
Germaneau RF.
Navarro O.
Stevens ED.
Nolan SP.
Organometallics
2002,
21:
5470
<A NAME="RC03808SS-105">105 </A>
Viciu MS.
Kissling RM.
Stevens ED.
Nolan SP.
Org.
Lett.
2002,
4:
2229
<A NAME="RC03808SS-106">106 </A>
Viciu MS.
Kelly RA.
Stevens ED.
Naud F.
Studer M.
Nolan SP.
Org. Lett.
2003,
5:
1479
<A NAME="RC03808SS-107">107 </A>
Navarro O.
Marion N.
Scott NM.
González J.
Amoroso D.
Bell A.
Nolan SP.
Tetrahedron
2005,
61:
9716
<A NAME="RC03808SS-108">108 </A>
Marion N.
Navarro O.
Mei J.
Stevens ED.
Scott NM.
Nolan SP.
J. Am. Chem. Soc.
2006,
128:
4101
<A NAME="RC03808SS-109">109 </A>
Navarro O.
Marion N.
Mei J.
Nolan SP.
Chem. Eur. J.
2006,
12:
5142
<A NAME="RC03808SS-110">110 </A>
Stauffer SR.
Hartwig JF.
J. Am. Chem. Soc.
2003,
125:
6977
<A NAME="RC03808SS-111">111 </A>
Titcomb LR.
Caddick S.
Cloke FGN.
Wilson DJ.
McKerrecher D.
Chem. Commun.
2001,
1388
<A NAME="RC03808SS-112">112 </A>
Organ MG.
Comer E.
Chem. Eur. J.
2005,
11:
7223
<A NAME="RC03808SS-113">113 </A>
Comer E.
Organ MG.
J. Am. Chem. Soc.
2005,
127:
8160
<A NAME="RC03808SS-114">114 </A>
Shore G.
Morin S.
Mallik D.
Organ MG.
Chem. Eur. J.
2008,
14:
1351
<A NAME="RC03808SS-115">115 </A>
Barluenga J.
Fernandez MA.
Aznar F.
Valdes C.
Chem. Eur. J.
2005,
11:
2276
<A NAME="RC03808SS-116">116 </A>
Lerma IC.
Cawley MJ.
Arentsen K.
Scott JS.
Pearlson SE.
Hayler J.
Caddick S.
J. Organomet. Chem.
2005,
690:
5841
<A NAME="RC03808SS-117">117 </A>
Ananikov VP.
Musaev DG.
Morokuma KJ.
J. Am. Chem. Soc.
2002,
124:
2839
<A NAME="RC03808SS-118">118 </A>
Ananikov VP.
Musaev DG.
Morokuma KJ.
Organometallics
2005,
24:
715
<A NAME="RC03808SS-119">119 </A>
Chin W.
Mons M.
Dognon J.-P.
Mirasol R.
Chass G.
Dimicoli I.
Piuzzi F.
Butz P.
Tardivel B.
Compagnon I.
von Helden G.
Meijer G.
J. Phys. Chem. A
2005,
109:
5281
<A NAME="RC03808SS-120">120 </A>
Chass GA.
Mirasol RS.
Setiadi DH.
Tang T.-H.
Chin W.
Mons M.
Dimicoli I.
Dognon J.-P.
Viskolcz B.
Lovas S.
Penke B.
Csizmadia IG.
J. Phys. Chem. A
2005,
109:
5289
<A NAME="RC03808SS-121">121 </A>
Chass GA.
Marai CNJ.
Harrison AG.
Csizmadia KJ.
J.
Phys. Chem. A
2002,
106:
9695
<A NAME="RC03808SS-122">122 </A>
Richardson TB.
de Gala S.
Crabtree RH.
Siegbahn PEM.
J.
Am. Chem. Soc.
1995,
117:
12875
<A NAME="RC03808SS-123">123 </A>
Robertson KN.
Knop O.
Cameron TS.
Can.
J. Chem.
2003,
81:
727
<A NAME="RC03808SS-124">124 </A>
Alkorta M.
Elguero J.
Grabowski SJ.
J.
Phys. Chem. A
2008,
112:
2721
<A NAME="RC03808SS-125">125 </A>
Frisch MJ.
Trucks GW.
Schlegel HB.
Scuseria GE.
Robb MA.
Cheeseman JR.
Montgomery JA.
Vreven JT.
Kudin KN.
Burant JC.
Millam JM.
Iyengar SS.
Tomasi J.
Barone V.
Mennucci B.
Cossi M.
Scalmani G.
Rega N.
Petersson GA.
Nakatsuji H.
Hada MEM.
Toyota K.
Fukuda R.
Hasegawa J.
Ishida M.
Nakajima T.
Honda Y.
Kitao O.
Nakai H.
Klene M.
Li X.
Knox JE.
Hratchian HP.
Cross JB.
Adamo C.
Jaramillo J.
Gomperts R.
Stratmann RE.
Yazyev O.
Austin AJ.
Cammi R.
Pomelli C.
Ochterski JW.
Ayala PY.
Morokuma K.
Voth GA.
Salvador P.
Dannenberg JJ.
Zakrzewski VG.
Dapprich S.
Daniels AD.
Strain MC.
Farkas O.
Malick DK.
Rabuck AD.
Raghavachari K.
Foresman JB.
Ortiz JV.
Cui Q.
Baboul AG.
Clifford S.
Cioslowski J.
Stefanov BB.
Liu G.
Liashenko A.
Piskorz P.
Komaromi I.
Martin RL.
Fox DJ.
Keith T.
Al-Laham MA.
Peng CY.
Nanayakkara A.
Challacombe M.
Gill PMW.
Johnson B.
Chen W.
Wong MW.
Gonzalez C.
Pople JA.
Gaussian
03, revision B.02
Gaussian, Inc.;
Pittsburgh
(PA):
2003.
<A NAME="RC03808SS-126">126 </A>
Godbout N.
Salahub DR.
Andzelm J.
Wimmer E.
Can. J. Chem.
1992,
70:
560
<A NAME="RC03808SS-127">127 </A>
Becke AD.
J.
Chem. Phys.
1993,
98:
5648
<A NAME="RC03808SS-128">128 </A>
Lee C.
Yang W.
Parr RG.
Phys.
Rev. B.
1988,
37:
785
<A NAME="RC03808SS-129">129 </A>
Miertus S.
Scrocco E.
Tomasi J.
Chem.
Phys.
1981,
55:
117
<A NAME="RC03808SS-130">130 </A>
Barone V.
Cossi M.
Tomasi J.
J.
Chem. Phys.
1997,
107:
3210
<A NAME="RC03808SS-131">131 </A>
Barone V.
Cossi M.
J. Phys. Chem. A.
1998,
120:
1995
<A NAME="RC03808SS-132">132 </A>
Mucsi Z.
Szabó A.
Hermecz I.
Kucsman Á.
Csizmadia IG.
J. Am. Chem. Soc.
2005,
127:
7615
<A NAME="RC03808SS-133">133 </A>
Wulf ORUL.
Hendericks SB.
J.
Am. Chem. Soc.
1936,
58:
2287
<A NAME="RC03808SS-134">134 </A>
Tamres M.
J.
Am. Chem. Soc.
1952,
74:
3375
<A NAME="RC03808SS-135">135 </A>
Burkley SK.
Petsko GA.
Adv. Protein Chem.
1988,
39:
125
<A NAME="RC03808SS-136">136 </A>
Steiner T.
Acta
Crystallogr., Sect. D
1998,
54:
584
<A NAME="RC03808SS-137">137 </A>
Steiner T.
Koellner G.
J. Mol. Biol.
2001,
305:
535
<A NAME="RC03808SS-138">138 </A>
Duan G.
Smith VH.
Weaver DF.
Chem. Phys. Lett.
1999,
310:
323
<A NAME="RC03808SS-139">139 </A>
Duan G.
Smith VH.
Weaver DF.
Int. J. Quantum Chem.
2000,
80:
44
<A NAME="RC03808SS-140">140 </A>
Bader RFW.
Acc. Chem. Res.
1985,
18:
9
<A NAME="RC03808SS-141">141 </A>
Bader RFW.
Atoms in Molecules,
A Quantum Theory
Clarendon Press;
Oxford
UK:
1990.
<A NAME="RC03808SS-142">142 </A>
Matta CF.
Hernandez-Trujillo J.
Tang T.-H.
Bader RFW.
Chem. Eur.
J.
2003,
9:
1940
<A NAME="RC03808SS-143">143 </A>
Popelier PLA.
J. Phys. Chem. A
1998,
102:
1873
<A NAME="RC03808SS-144">144 </A>
Bader RFW.
Fang D.-C.
J. Chem.
Theory Comput.
2005,
1:
403
<A NAME="RC03808SS-145">145 </A>
Platts JA.
Howard ST.
Bracke BRF.
J. Am. Chem. Soc.
1996,
118:
2726
<A NAME="RC03808SS-146">146 </A>
Platts JA.
Howard ST.
J. Chem. Phys.
1996,
105:
4668
<A NAME="RC03808SS-147">147 </A>
Koch U.
Popelier PLA.
J. Phys.
Chem.
1995,
99:
9747
<A NAME="RC03808SS-148">148 </A>
Gatti C.
Saunders VR.
Roetti C.
J.
Chem. Phys.
1994,
101:
10686
<A NAME="RC03808SS-149">149 </A>
Espinosa E.
Molins E.
Lecomte C.
Chem.
Phys. Lett.
1998,
285:
170
<A NAME="RC03808SS-150">150 </A>
Espinosa E.
Souhassou M.
Lachekar H.
Lecomte C.
Acta Crystallogr., Sect. B
1999,
55:
563
<A NAME="RC03808SS-151">151 </A>
Rendeif EE.
Dahaoui S.
Renali-Cherif N.
Lecomte C.
Acta Crystallogr., Sect. B
2007,
63:
448
<A NAME="RC03808SS-152">152 </A>
Albert S.
Pillet S.
Lecomte C.
Pradel A.
Ribes M.
Acta Crystallogr.,
Sect. B
2008,
64:
1
<A NAME="RC03808SS-153">153 </A>
Aubert E.
Lecomte C.
J. Appl. Crystallogr.
2007,
40:
1153
<A NAME="RC03808SS-154">154 </A>
Koritsansky TS.
Coppens P.
Chem. Rev.
2001,
101:
1583
<A NAME="RC03808SS-155">155 </A>
Flaig R.
Koritsanszky TS.
Dittrich B.
Wagner A.
Luger P.
J.
Am. Chem. Soc.
2002,
124:
3407
<A NAME="RC03808SS-156">156 </A>
Lee C.-R.
Tang T.-H.
Chen L.
Wang Y.
Chem. Eur. J.
2003,
9:
3112
<A NAME="RC03808SS-157">157 </A>
Guillot B.
Jelsch C.
Podjarny A.
Lecomte C.
Acta Crystallogr., Sect. D
2008,
64:
567
<A NAME="RC03808SS-158">158 </A>
Tang T.-H.
Deretey E.
Knak Jensen SJ.
Csizmadia IG.
Eur.
Phys. J., D: Atom Mol. Opt. Phys.
2006,
37:
217
<A NAME="RC03808SS-159">159 </A>
Cortes-Guzman F.
Richard RFW.
Coord.
Chem. Rev.
2005,
249:
633
