-
3
-
-
0030590426
-
-
(a) Howard, J. A. K.; Hoy, V. J.; O'Hagan, D.; Smith, G. T. Tetrahedron 1996, 52, 12613.
-
(1996)
Tetrahedron
, vol.52
, pp. 12613
-
-
Howard, J.A.K.1
Hoy, V.J.2
O'Hagan, D.3
Smith, G.T.4
-
5
-
-
0034600791
-
-
(c) Takemura, H.; Kon, N.; Yasutake, M.; Nakashima, S.; Shinmyozu, T.; Inazu, T. Chem. Eur. J. 2000, 6, 2334.
-
(2000)
Chem. Eur. J.
, vol.6
, pp. 2334
-
-
Takemura, H.1
Kon, N.2
Yasutake, M.3
Nakashima, S.4
Shinmyozu, T.5
Inazu, T.6
-
6
-
-
0000243556
-
-
(d) Brammer, L.; Bruton, E. A.; Sherwood, P. Cryst. Growth Des. 2001, 1, 277.
-
(2001)
Cryst. Growth Des.
, vol.1
, pp. 277
-
-
Brammer, L.1
Bruton, E.A.2
Sherwood, P.3
-
7
-
-
3242877691
-
-
(e) Hyla-Kryspin, I.; Haufe, G.; Grimme, S. Chem. Eur. J. 2004, 10, 3411.
-
(2004)
Chem. Eur. J.
, vol.10
, pp. 3411
-
-
Hyla-Kryspin, I.1
Haufe, G.2
Grimme, S.3
-
9
-
-
0034716326
-
-
An alternative description of the attractive interaction between N-H and F-C dipoles has recently been proposed: (a) Snyder, J. P.; Chandrakumar, N. S.; Sato, H.; Lankin, D. C. J. Am. Chem. Soc. 2000, 122, 544.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 544
-
-
Snyder, J.P.1
Chandrakumar, N.S.2
Sato, H.3
Lankin, D.C.4
-
10
-
-
0037126202
-
-
(b) Lankin, D. C.; Grunewald, G. L.; Romero, F. A.; Oren, I. Y.; Snyder, J. P. Org. Lett. 2002, 4, 3557.
-
(2002)
Org. Lett.
, vol.4
, pp. 3557
-
-
Lankin, D.C.1
Grunewald, G.L.2
Romero, F.A.3
Oren, I.Y.4
Snyder, J.P.5
-
13
-
-
0030731024
-
-
(a) Borwick, S. J.; Howard, J. A. K.; Lehmann, C. W.; O'Hagan, D. Acta Crystallogr. E 1997, 53, 124.
-
(1997)
Acta Crystallogr. E
, vol.53
, pp. 124
-
-
Borwick, S.J.1
Howard, J.A.K.2
Lehmann, C.W.3
O'Hagan, D.4
-
14
-
-
24644467897
-
-
(b) Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403.
-
(1997)
Chem. Commun.
, pp. 2403
-
-
Weiss, H.-C.1
Boese, R.2
Smith, H.L.3
Haley, M.M.4
-
15
-
-
0032475420
-
-
(c) Thalladi, V. K.; Weiss, H.-C.; Bläser, D.; Boese, R.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 8702.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 8702
-
-
Thalladi, V.K.1
Weiss, H.-C.2
Bläser, D.3
Boese, R.4
Nangia, A.5
Desiraju, G.R.6
-
16
-
-
0033526306
-
-
(d) Barbarich, T. J.; Rithner, C. D.; Miller, S. M.; Anderson, O. P.; Strauss, S. H. J. Am. Chem. Soc. 1999, 121, 4280.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 4280
-
-
Barbarich, T.J.1
Rithner, C.D.2
Miller, S.M.3
Anderson, O.P.4
Strauss, S.H.5
-
17
-
-
14644411793
-
-
For a recent review of fluorine in crystal engineering, see: (e) Reichenbächer, K.; Süss, H. I.; Hulliger, J. Chem. Soc. Rev. 2005, 34, 22.
-
(2005)
Chem. Soc. Rev.
, vol.34
, pp. 22
-
-
Reichenbächer, K.1
Süss, H.I.2
Hulliger, J.3
-
19
-
-
0141521505
-
-
Bochmann, M.; Lancaster, S. J.; Hannant, M. D.; Rodriguez, A.; Schormann, M.; Walker, D. A.; Woodman, T. J. Pure Appl. Chem. 2003, 75, 1183.
-
(2003)
Pure Appl. Chem.
, vol.75
, pp. 1183
-
-
Bochmann, M.1
Lancaster, S.J.2
Hannant, M.D.3
Rodriguez, A.4
Schormann, M.5
Walker, D.A.6
Woodman, T.J.7
-
22
-
-
0000711729
-
-
For example, see: (a) Lesley, M. J. G.; Woodward, A.; Taylor, N. J.; Marder, T. B.; Cazenobe, I.; Ledoux, I.; Zyss, J.; Thornton, A.; Bruce, D. W.; Kakkar, A. K. Chem. Mater. 1998, 10, 1355.
-
(1998)
Chem. Mater.
, vol.10
, pp. 1355
-
-
Lesley, M.J.G.1
Woodward, A.2
Taylor, N.J.3
Marder, T.B.4
Cazenobe, I.5
Ledoux, I.6
Zyss, J.7
Thornton, A.8
Bruce, D.W.9
Kakkar, A.K.10
-
23
-
-
0000863229
-
-
(b) Jacobsen, H.; Berke, H.; Döring, S.; Kehr, G.; Erker, G.; Fröhlich, R.; Meyer, O. Organometallics 1999, 18, 1724.
-
(1999)
Organometallics
, vol.18
, pp. 1724
-
-
Jacobsen, H.1
Berke, H.2
Döring, S.3
Kehr, G.4
Erker, G.5
Fröhlich, R.6
Meyer, O.7
-
24
-
-
0034326967
-
-
(c) Bergquist, C.; Bridgewater, B. M.; Harlan, C. J.; Norton, J. R.; Friesner, R. A.; Parkin, G. J. Am. Chem. Soc. 2000, 122, 10581.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 10581
-
-
Bergquist, C.1
Bridgewater, B.M.2
Harlan, C.J.3
Norton, J.R.4
Friesner, R.A.5
Parkin, G.6
-
25
-
-
0034743006
-
-
(d) Beckett, M. A.; Brassington, D. S.; Light, M. E.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 2001, 1768.
-
(2001)
J. Chem. Soc., Dalton Trans.
, pp. 1768
-
-
Beckett, M.A.1
Brassington, D.S.2
Light, M.E.3
Hursthouse, M.B.4
-
26
-
-
0037182793
-
-
(e) Drewitt, M. J.; Niedermann, M.; Kumar, R.; Baird, M. C. Inorg. Chim. Acta 2002, 335, 43.
-
(2002)
Inorg. Chim. Acta
, vol.335
, pp. 43
-
-
Drewitt, M.J.1
Niedermann, M.2
Kumar, R.3
Baird, M.C.4
-
27
-
-
12344290570
-
-
(f) Vagedes, D.; Erker, G.; Kehr, G.; Bergander, K.; Kataeva, O.; Fröhlich, R.; Grimme, S.; Mück-Lichtenfeld, C. Dalton Trans. 2003, 1337.
-
(2003)
Dalton Trans.
, pp. 1337
-
-
Vagedes, D.1
Erker, G.2
Kehr, G.3
Bergander, K.4
Kataeva, O.5
Fröhlich, R.6
Grimme, S.7
Mück-Lichtenfeld, C.8
-
30
-
-
0037666885
-
-
Lancaster, S. J.; Rodriguez, A.; Lara-Sanchez, A.; Hannant, M. D.; Walker, D. A.; Hughes, D. L.; Bochmann, M. Organometallics 2002, 21, 451.
-
(2002)
Organometallics
, vol.21
, pp. 451
-
-
Lancaster, S.J.1
Rodriguez, A.2
Lara-Sanchez, A.3
Hannant, M.D.4
Walker, D.A.5
Hughes, D.L.6
Bochmann, M.7
-
31
-
-
0042890337
-
-
Lancaster, S. J.; Mountford, A. J.; Hughes, D. L.; Schormann, M.; Bochmann, M. J. Organomet. Chem. 2003, 680, 193.
-
(2003)
J. Organomet. Chem.
, vol.680
, pp. 193
-
-
Lancaster, S.J.1
Mountford, A.J.2
Hughes, D.L.3
Schormann, M.4
Bochmann, M.5
-
33
-
-
0037999878
-
-
3. For comparison, they also prepared (2,3-dihydro-1H-indole)tris(pentafluorophenyl)boron, which exhibits a bifurcated intramolecular hydrogen-bonding motif closely related to those in this study: Guidotti, S.; Camurati, I.; Focante, F.; Angellini, L.; Moscardi, G.; Resconi, L.; Leardini, R.; Nanni, D.; Mercandelli, P.; Sironi, A.; Beringhelli, T.; Maggioni, D. J. Org. Chem. 2003, 68, 5445.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 5445
-
-
Guidotti, S.1
Camurati, I.2
Focante, F.3
Angellini, L.4
Moscardi, G.5
Resconi, L.6
Leardini, R.7
Nanni, D.8
Mercandelli, P.9
Sironi, A.10
Beringhelli, T.11
Maggioni, D.12
-
36
-
-
0032556479
-
-
2O: Danopoulos, A. A.; Galsworthy, J. R.; Green, M. L. H.; Cafferkey, S.; Doerrer, L. H.; Hursthouse, M. B. Chem. Commun. 1998, 2529.
-
(1998)
Chem. Commun.
, pp. 2529
-
-
Danopoulos, A.A.1
Galsworthy, J.R.2
Green, M.L.H.3
Cafferkey, S.4
Doerrer, L.H.5
Hursthouse, M.B.6
-
37
-
-
18444390841
-
-
2O: Coles, S. J.; Hursthouse, M. B.; Beckett, M. A.; Dutton, M. Acta Crystallogr. E 2003, 59, 1354.
-
(2003)
Acta Crystallogr. E
, vol.59
, pp. 1354
-
-
Coles, S.J.1
Hursthouse, M.B.2
Beckett, M.A.3
Dutton, M.4
-
38
-
-
0004057754
-
-
Kaminsky, W., Ed.; Springer Verlag: Berlin
-
2O: Lancaster, S. J.; O'Hara, S. M.; Bochmann, M. In Metalorganic Catalysts for Synthesis and Polymerization; Kaminsky, W., Ed.; Springer Verlag: Berlin, 2000.
-
(2000)
Metalorganic Catalysts for Synthesis and Polymerization
-
-
Lancaster, S.J.1
O'Hara, S.M.2
Bochmann, M.3
-
39
-
-
0035851947
-
-
Beringhelli, T.; Maggioni, D.; D'Alfonso, G. Organometallics 2001, 20, 4927.
-
(2001)
Organometallics
, vol.20
, pp. 4927
-
-
Beringhelli, T.1
Maggioni, D.2
D'Alfonso, G.3
-
40
-
-
33645361898
-
-
See: Reference 21
-
3Al in a light petroleum solution followed by removal of the volatiles and resuspension in light petroleum. See: Reference 21.
-
-
-
-
41
-
-
33645364862
-
-
U.S. Patent 5,602,269, 1997
-
Biagini, P.; Lugli, G.; Abis, L.; Andreussi, P. U.S. Patent 5,602,269, 1997.
-
-
-
Biagini, P.1
Lugli, G.2
Abis, L.3
Andreussi, P.4
-
42
-
-
0345267184
-
-
Lee, C. H.; Lee, S. J.; Park, J. W.; Kim, K. H.; Lee, B. Y.; Oh, J. S. J. Mol. Catal., A 1998, 132, 231.
-
(1998)
J. Mol. Catal., A
, vol.132
, pp. 231
-
-
Lee, C.H.1
Lee, S.J.2
Park, J.W.3
Kim, K.H.4
Lee, B.Y.5
Oh, J.S.6
-
44
-
-
0001069741
-
-
Belgardt, T.; Storre, J.; Roesky, H. W.; Noltemeyer, M.; Schmidt, H.-G. Inorg. Chem. 1995, 34, 3821.
-
(1995)
Inorg. Chem.
, vol.34
, pp. 3821
-
-
Belgardt, T.1
Storre, J.2
Roesky, H.W.3
Noltemeyer, M.4
Schmidt, H.-G.5
-
46
-
-
0034605461
-
-
LaPointe, R. E.; Roof, G. R.; Abboud, K. A.; Klosin, J. J. Am. Chem. Soc. 2000, 122, 9560.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 9560
-
-
LaPointe, R.E.1
Roof, G.R.2
Abboud, K.A.3
Klosin, J.4
-
47
-
-
12344300164
-
-
Schatte, G.; Chivers, T.; Tuononen, H. M.; Suontamo, R.; Laitinen, R.; Valkonen, J. Inorg. Chem. 2005, 44, 443.
-
(2005)
Inorg. Chem.
, vol.44
, pp. 443
-
-
Schatte, G.1
Chivers, T.2
Tuononen, H.M.3
Suontamo, R.4
Laitinen, R.5
Valkonen, J.6
-
48
-
-
1642308746
-
-
Rossmeier, T.; Reil, M.; Korber, N. Inorg. Chem. 2004, 43, 2206.
-
(2004)
Inorg. Chem.
, vol.43
, pp. 2206
-
-
Rossmeier, T.1
Reil, M.2
Korber, N.3
-
49
-
-
0001774339
-
-
3 crystallizes with two independent molecules, neither of which exhibits close intramolecular H⋯F contacts, but there is an intermolecular interaction at 2.39 Å: Bradley, D. C.; Hursthouse, M. B.; Motevalli, M.; Zheng, D. H. J. Chem. Soc., Chem. Commun. 1991, 7.
-
(1991)
J. Chem. Soc., Chem. Commun.
, pp. 7
-
-
Bradley, D.C.1
Hursthouse, M.B.2
Motevalli, M.3
Zheng, D.H.4
-
50
-
-
0001711157
-
-
Remarkably similar bifurcated intramolecular hydrogen-bonding arrangements were observed in 2,6-bis(2,6-difluorophenyl)piperidines: Pham, M.; Gdaniec, M.; Poloñski, T. J. Org. Chem. 1998, 63, 3731.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 3731
-
-
Pham, M.1
Gdaniec, M.2
Poloñski, T.3
-
51
-
-
33748642371
-
-
3 crystallizes with two independent molecules, each of which has one medium-length intramolecular H⋯F contact (2.337 and 2.357 Å): Bradley, D. C.; Harding, I. S.; Keefe, A. D.; Motevalli, M.; Zheng, D. H. J. Chem. Soc., Dalton Trans. 1996, 3931.
-
(1996)
J. Chem. Soc., Dalton Trans.
, pp. 3931
-
-
Bradley, D.C.1
Harding, I.S.2
Keefe, A.D.3
Motevalli, M.4
Zheng, D.H.5
-
52
-
-
33645373230
-
-
See: Reference 7e and references therein
-
Favorable intra- and intermolecular interactions between the complementary quadrupoles of fluoroaryl and hydroaryl groups are well-known. See: Reference 7e and references therein.
-
-
-
-
53
-
-
4544379892
-
-
For an estimation of the strength of a O-H⋯F-C hydrogen bond, see: Takemura, H.; Kotoku, M.; Yasutake, M.; Sinmyozu, T. Eur. J. Org. Chem. 2004, 2019.
-
(2004)
Eur. J. Org. Chem.
, pp. 2019
-
-
Takemura, H.1
Kotoku, M.2
Yasutake, M.3
Sinmyozu, T.4
-
55
-
-
33645373772
-
-
Lancaster, S. J. http://www.syntheticpages.org/pages/215.
-
-
-
Lancaster, S.J.1
-
58
-
-
0001086706
-
-
Kluwer Academic Publishers: Dordrecht, The Netherlands
-
International Tables for X-ray Crystallography; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; Vol. C, pp 193, 219, and 500.
-
(1992)
International Tables for X-ray Crystallography
, vol.C
, pp. 193
-
-
-
59
-
-
51149214796
-
-
Anderson, S. N.; Richards, R. L.; Hughes, D. L. J. Chem. Soc., Dalton Trans. 1986, 245.
-
(1986)
J. Chem. Soc., Dalton Trans.
, pp. 245
-
-
Anderson, S.N.1
Richards, R.L.2
Hughes, D.L.3
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