Using hydrogen-bonds and herringbone packing to design interfaces of 4,4'-disubstituted meso-hydrobenzoin crystals. The importance of recognizing unfavorable packing motifs

Journal of the American Chemical Society

Volumn 120, Issue 1, 1998, Pages 96-104

  Swift, Jennifer A ^a   Pal, Rajib ^a   McBride, J Michael ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIN; STILBENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 0032515417     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9730066     Document Type: Article

References (46)

1. Numerous examples exist in the literature. For an overview, see: (a) Ulman, A. Ultrathin Organic Films from Langmuir Blodgett to Self-Assembly; Academic Press: San Diego, CA, 1991.
2. Gavezzotti, A. Acc. Chem. Res. 1994, 27, 309-314.
3. (a) McBride, J. M.; Bertman, S. B.; Semple, T. C. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 4743-4746.
4. (b) McBride, J. M.; Bertman, S. B.; Cioffi, D. Z.; Segmuller, B. E.; Weber, B. A. Mol. Cryst. Liq. Cryst. Nonlin. Opt. 1988, 161, 1-24.
5. (c) Bertman, S. B. Ph.D. Thesis, Yale University, 1990.
6. Pennington, W. T.; Chakraborty, S.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1988, 110, 6498-6504.
7. The H⋯O bond distance is 1.94 Å (O⋯O distance, 2.80 Å); the O-H⋯O bond angle is 172°.
8. (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
9. (b) Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989, 621-623.
10. (c) Gavezzotti, A. Chem. Phys. Lett. 1989, 161, 67-72.
11. Center-center distance = 5.08 Å.
12. Dihedral angle = 91.1°; center-center distance = 5.15 Å.
13. Karlsson, O.; Lundquist, K.; Stomberg, R. Acta Chem. Scand. 1990, 44, 617-624. The paper reports a completely different packing for mesohydroveratroin, where additional methoxyl groups in the 3 and 3′ positions would disrupt the herringbone packing.
14. Personal communication from R. Stomberg.
15. Note that any extra entropy of melting for MeO-mHB, due to the freeing of torsional degrees of freedom of the methoxyl group, must tend to lower its melting point. Of course, analyzing melting points in terms of group interactions has only qualitative significance, since melting points compare solids with the corresponding liquids, not with gas-phase molecules. Although liquids should be less able to optimize intermolecular attractions than solids, they do not eliminate them.
16. Several of these crystals were also used in an AFM study of crystal dissolution. Results to be published.
17. Fieser, L. F.; Williamson, K. L. Organic Experiments, 3rd ed.; D. C. Heath: Lexington, MA, 1975.
18. Trahanovsky, W. S.; Gilmore, J. R.; Heaton, P. C. J. Org. Chem. 1973, 38, 760-763.
19. Grimshaw, J.; Ramsey, J. S. J. Chem. Soc. C. 1966, 653-655.
20. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. DIRDIF94: The DIRDIF-94 program system; Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
21. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography, Vol. IV; The Kynoch Press: Birmingham, England, 1961; Table 2.2A.
22. Creagh, D. C.; Hubbell, J. H. International Tables for Crystallography, Vol C; Wilson, A. J. C., Ed.; Kluwer: Boston, MA, 1992; Table 4.2.4.3, pages 200-206.
23. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation, 1985 and 1992.
24. Allen, F. H.; Kennard, O. Chem. Des. Automat. News. 1993, 8 (1), 31-37.
25. ortho angles are the following: H, 76.7°; F, 78.8°; Me, 83.2°; MeO, 78.1°; Cl, 74.8°, 70.8°, 74.0°, 72.1°; Br, 64.1°, 76.5°, 68.8°, 70.7°.
26. Dunitz, J.; Taylor, R. Chem. Eur. J. 1997, 3, 89.
27. (a) Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063-5070.
28. (b) Desiraju, G. R. Acc. Chem. Res 1996, 29, 441-449.
29. Of course the increase in melting point is also due in some measure to increased intralayer cohesion.
30. Indirect AFM evidence suggests that twin domains can be as thin as a single molecular layer. Manuscript in preparation.
31. To measure ribbon width the nonhydrogen atoms are projected on the plane analogous to (100) of mHB. The most remote atom, which defines the edge of the ribbon, is C(10). In Br-mHB, it is O(2).
32. In mHB, the hydrogen-bonded O-O distance is 2.80 Å, in Cl-mHB the three O⋯O distances range from 2.79 to 2.80 Å.
33. CSD Refcodes: HQNLSE, JICRAO, SEZLIS, SORYIH, THAMCU, VEWRIY, WECBOV, YILTUI.
34. Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647.
35. Desiraju, G. R. Organic Solid State Chemistry, Studies in Organic Chemistry, vol 32; Eisevier: New York, 1987.
36. Distances (Cl⋯Cl) and angles: 3.40 Å, C-Cl(2)⋯Cl(1) 146.89°, Cl(2)⋯Cl(1)-C, 137.66°; 3.49 Å, C-Cl(4)⋯Cl(4), 144.93°; 3.76 Å, C-Cl-(4)⋯Cl(3), 126.84°; Cl(4)⋯Cl(3)-C, 134.71°.
37. C-Cl⋯Cl angles range from 90 to 107°; C-Cl⋯Cl-C torsional angles from 0 to 13°.
38. H⋯O 1.92-1.96 Å; O⋯O 2.77-2.80 Å; O-H⋯O 163-167°.
39. CSD Refcodes: BAJVOX, BOCHOO, BOTDET, DEFSUC, FAT-JUF, JEWXUE, KONVEO, LINMIE, PACFOL, SAXITB, YISZUV.
40. Slicing to form the ribbon preserves three of four short antiparallel C-Br⋯Br-C contacts with Br⋯Br distances 3.76-4.34 Å and C-Br⋯ Br angles 122-134°.
41. Slicing to form the ribbon removes the shortest three parallel C-Br⋯Br-C contacts with Br⋯Br distances 4.52-4.87 Å, C-Bp⋯Br angles 91-100°; C-Br⋯Br-C torsional angles 0-8°.
42. Similarity of the b cell parameters (Table 1) is purely accidental.
43. The choice of occupancy is not completely arbitrary, since individual molecules must remain meso.
44. O⋯O distances: 2.86, 3.02, 2.86 Å. C-O⋯O angles: 136°, 144°, 107°. C-C-O⋯O torsional angles: -76°, 103°, -87°. Note that a symmetry dyad of the C2/c space group passes through the middle of the C-shaped chain, meaning that the chain could change its polarity by rotation of the four OH groups. The H-atoms are almost certainly disordered, perhaps dynamically.
45. The new hydrogen bond has O⋯O distance 3.14 Å, C-O⋯O angle 95°, C-C-O⋯O torsion 92°.
46. For example, 11-bromoundecanoyl peroxide melts 20°C higher than isomorphous 11-bromoundecanoyl dodecanoyl peroxide (72.3-75.7°C vs 53 0-53.8°C); even-numbered α,ω-dibromoalkanes melt 20-50°C higher than their dimethyl analogues. There are many counter examples, such as the odd-numbered α,ω-dibromoalkanes, where the melting points differ by only a few degrees. See: Breusch, F. L. Fort. Chem. Forsch. 1969, 12, 119 and ref 3c.