J. Michael McBride at 65 - An appreciation

Crystal Growth and Design

Volumn 5, Issue 6, 2005, Pages 2022-2035

  Hollingsworth, Mark D ^a   Swift, Jennifer A ^b   Kahr, Bart ^c  

^a KANSAS STATE UNIVERSITY   (United States)

^b GEORGETOWN UNIVERSITY   (United States)

^c UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27744561447     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg0505362     Document Type: Review

References (107)

1. Kurt Vonnegut made Mike's hometown famous when he imagined a 1950s Lima science fair aspirant who was determined to show the "important services that acids...were performing every day for Humanity", but whose acid-laden car was disastrously rear-ended while leaving his driveway. With acids out of the hunt, the state competition in Cleveland was contested between two displays "about crystals and how they grow and why they grow." Needless to say, Mike survived Lima with his love of crystals intact. See Vonnegut, K. Hocus Pocus; Berkley Books: New York, 1991; pp 31-38.
2. McBride, J. M. In P.D. and the Bartlett Group at Harvard 1934-1974; McBride, J. M., Ed.; P. D. Bartlett: Cambridge, MA, 1975; pp 207-211.
3. McBride, J. M. Caged radical pairs and A further study of the norbornane peresters. Ph.D. Thesis, Harvard University, Cambridge, MA, 1966.
4. This incorporates Bartlett, P. D.; McBride, J. M. A Further Study of the exo- and endo-2-carbo-t-butylperoxynorbornanes. J. Am. Chem. Soc. 1965, 87, 1727-1733.
5. McBride, J. M. The Gerhard M. J. Schmidt Prize and Memorial Lecture; The Weizmann Institute of Science: Rehovot, Israel, March 6, 1990.
6. Brandon, R. W.; Closs, G. L.; Hutchison, C. A., Jr. Paramagnetic resonance in oriented ground-state triplet molecules. J. Chem. Phys. 1962, 37, 1878-1879.
7. Bartlett, P. D.; McBride, J. M. Configuration, conformation and spin in radical pairs. Pure Appl. Chem. 1967, 15, 89-107.
8. McBride, J. M. Chemistry. In Science at Yale; Altman, S., Ed.; Yale University: New Haven, CT, 2002.
9. Berson, J. A.; Bushby, R. J.; McBride, J. M.; Tremelling, M. 2-Isopropylidenecyclopentane-1,3-diyl. Preparation, properties, and reactions of a distorted trimethylenemethane. Direct evidence for a triplet reaction. J. Am. Chem. Soc. 1971, 93, 1544-1546. For years, Mike and Jerry shared weekly group meetings.
10. Platz, M. S.; McBride, J. M.; Little, R. D.; Harrison, J. J.; Shaw, A.; Potter, S. E.; Berson, J. A. Triplet ground states of trimethylenemethanes. J. Am. Chem. Soc. 1976, 98, 5725-5726.
11. 2. Cryst. Struct. Commun. 1980, 9, 85-90.
12. Saunders, M.; Berger, R.; Jaffe, A.; McBride, J. M.; O'Neill, J.; Breslow, R.; Hoffman, J. M., Jr.; Perchonock, C.; Wasserman, E.; Hutton, R. S.; Kuck, V. J. Unsubstituted cyclopentadienyl cation, a ground-state triplet. J. Am. Chem. Soc. 1973, 95, 3017-3018.
13. 14-15
14. McBride, J. M.; Keehn, P. M.; Wasserman, H. H. Thermochemistry of syn- and anti-[2.2](1,4)naphthalenophane and dibenzoequinine. Strain energies. Tetrahedron Lett. 1969, 47, 4147-4150.
15. 2. Cryst. Struct. Commun. 1979, 8, 807-814.
16. 2Br. Cryst. Struct. Commun. 1979, 8, 799-805.
17. Malament, D. S.; McBride, J. M. α,α′- Dichloroazoalkanes. I. Synthesis: Stereospecificity and side reactions. The crystal structure of 1,1′-dichloro-1,1′-diphenyl-1,1′- azopropane. J. Am. Chem. Soc. 1970, 92, 4586-4593.
18. Malament, D. S.; McBride, J. M. α,α′- Dichloroazoalkanes. II. The mechanism of stereospecific synthesis and substitution. J. Am. Chem. Soc. 1970, 92, 4593-4598.
19. McBride, J. M. Rotational diffusion control of radical disproportionation in the solid-state photolysis of azobisisobutyronitrile. J. Am. Chem. Soc. 1971, 93, 6302-6303.
20. Jaffe, A. B.; Malament, D. S.; Slisz, E. P.; McBride, J. M. Solvent steric effects. III. Molecular and crystal structures of azobisisobutyronitrile and azobis-3-cyano-3-pentane. A structural deuterium isotope effect. J. Am. Chem. Soc. 1972, 94, 8515-8521.
21. Jaffe, A. B.; Skinner, K. J.; McBride, J. M. Solvent steric effects. II. The free-radical chemistry of azobisisobutyronitrile and azobis-3-cyano-3- pentane in viscous and crystalline media. J. Am. Chem. Soc. 1972, 94, 8510-8515.
22. Karch, N. J.; McBride, J. M. Solvent steric effects. VII. Lattice control of free radicals from the photolysis of crystalline acetyl benzoyl peroxide. J. Am. Chem. Soc. 1972, 94, 5092-5093.
23. Skinner, K. J.; Blaskiewicz, R. J.; McBride, J. M. Solvent steric effects. VI. Solid-state photolysis of azobis-3-phenyl-3-pentane. Crystal-lattice control of the stereochemistry of radical disproportionation. Isr. J. Chem. 1972, 10, 457-470.
24. Tremelling, M. J.; McBride, J. M. Solvent steric effects. V. Azobis-2-methyl-3-phenyl-2-butane. The absolute configuration of some derivatives of 2-methyl-3-phenylbutane. J. Org. Chem. 1972, 37, 1073-1075. Correction. J. Org. Chem. 1973, 38, 4217.
25. Jaffe, A.; McBride, J. M. Isotope studies of the reaction sites in AIBN photolysis. Solid Org. State 1974, 3, 16-22.
26. McBride, J. M. The role of local stress in solid-state radical reactions. Acc. Chem. Res. 1983, 16, 304-312.
27. Hollingsworth, M. D.; McBride, J. M. Photochemical mechanism in single crystals: FTIR studies of diacyl peroxides. In Adv. Photochem.; Volman, D. H., Hammond, G. S., Gollnick, K., Eds.; Wiley-Interscience: New York, 1990; Vol. 15, pp 279-379.
28. McBride, J. M. Overlap and the prevalence of banana bonds in free radicals and carbenes. J. Am. Chem. Soc. 1977, 99, 6760-6762.
29. Reichel, C. L.; McBride, J. M. Bent bonds in the bridgehead triptycyl radical. J. Am. Chem. Soc. 1977, 99, 6758-6760.
30. McBride, J. M.; Vary, M. W.; Whitsel, B. L. EPR studies of radical pairs. The benzoyloxy dilemma. ACS Symp. Ser. (Organic Free Radicals) 1978, 69, 208-223.
31. McBride, J. M.; Gisler, M. R. Isotopic and optical studies of the decomposition of crystalline dibenzoyl peroxide. Mol. Cryst. Liq. Cryst. 1979, 52, 121-132.
32. Vary, M. W.; McBride, J. M. Single-crystal EPR studies of radical pairs in dibenzoyl peroxide. Mol. Cryst. Liq. Cryst. 1979, 52, 133-144.
33. 2 of 110° much better than those of the other three candidates for the ground state (0°, 18°, and 35°).
34. Karch, N. J.; Koh, E. T.; Whitsel, B. L.; McBride, J. M. An X-ray and electron paramagnetic resonance structural investigation of oxygen discrimination during the collapse of methyl-benzoyloxy radical pairs in crystalline acetyl benzoyl peroxide. J. Am. Chem. Soc. 1975, 97, 6729-6743.
35. Peyerimhoff, S. D.; Skell, P. S.; May, D. D.; Buenker, R. J. Configuration interaction study of the three lowest electronic states in the formyl and acetyl radicals. J. Am. Chem. Soc. 1982, 104, 4515-4520.
36. 2•. J. Am. Chem. Soc. 1983, 105, 1459-1466.
37. McBride, J. M.; Vary, M. W. Radical pairs in crystalline dibenzoyl peroxide. Evidence for triplet ground states. Tetrahedron 1982, 38, 765-775. This article contains a particularly lucid rationale for Hund's Rule.
38. 2 ground state. Ph.D. Thesis, Yale University, New Haven, CT, 1986.
39. See Gavezzotti, A.; Bianchi, R. Potential-energy calculations and packing analysis for molecular motions in reactive diacyl peroxide crystals. Chem. Phys. Lett. 1986, 128, 295-299 for an analysis of free volume in this reaction cavity.
40. Kearsley, S. K.; McBride, J. M. Using molecular mechanics to model the movement and relaxation of radical pairs created by photolysis of single crystals of acetyl benzoyl peroxide (ABP). Mol. Cryst. Liq. Cryst. 1988, 156, 109-122.
41. Walter, D. W.; McBride, J. M. Neophyl rearrangements in crystalline bis(3,3,3-triphenylpropanoyl) peroxide. 2. Structural studies by X-ray and EPR. The mechanistic role of inert molecules. J. Am. Chem. Soc. 1981, 103, 7074-7084.
42. Walter, D. W.; McBride, J. M. Neophyl rearrangements in crystalline bis(3,3,3-triphenylpropanoyl) peroxide. 1. Dynamic studies by EPR. J. Am. Chem. Soc. 1981, 103, 7069-7073.
43. See Gavezzotti, A. Packing analysis in reactive crystals. The decomposition of bis(3,3,3-triphenylpropanoyl) peroxide in the solid state. Tetrahedron 1987, 43, 1241-1251 for a free volume analysis of this system.
44. Whitsel, B. L. The kinetics and structure of radical pairs: acetyl benzoyl peroxide. Ph.D. Thesis, Yale University, New Haven, CT, 1977.
45. Hollingsworth, M. D.; McBride, J. M. Infrared studies of long-range stress in solid-state peroxide photoreactions. Mol. Cryst. Liq. Cryst. 1988, 161, 25-41.
46. McBride, J. M. Radical-pair reactions in organic single crystals, In Static, Kinematic and Dynamic Aspects of Crystal and Molecular Structure; Riva, L., Ed.; 18th International School of Crystallography: Erice, Italy, 1991; pp 101-106.
47. Luty, T.; Eckhardt, C. J. General theoretical concepts for solid state reactions: Quantitative formulation of the reaction cavity, steric compression, and reaction-induced stress using an elastic multipole representation of chemical pressure. J. Am. Chem. Soc. 1995, 117, 2441-2452.
48. Thoreau, H. D. Walden; Random House: New York, 1937; p 4.
49. Segmuller, B. E. Diundecanoyl peroxide: EPR study and product analysis. Ph.D. Thesis, Yale University, New Haven, CT, 1982.
50. McBride, J. M. Analysis of local free volume in lamellar crystals: an aid for understanding radical mobility in solids. Mol. Cryst. Liq. Cryst. 1983, 96, 19-31.
51. McBride, J. M.; Segmuller, B. E.; Hollingsworth, M. D.; Mills, D. E.; Weber, B. A. Mechanical stress and reactivity in organic solids. Science 1986, 234, 830-835.
52. Hollingsworth, M. D. Infrared studies of carbon dioxide dimers as a probe of local stress in solid state peroxide reactions. Ph.D. Thesis, Yale University, New Haven, CT, 1986.
53. Hollingsworth, M. D.; McBride, J. M. Specific long-range effects on relaxation of local stress during a solid-state reaction. J. Am. Chem. Soc. 1985, 107, 1792-1793.
54. 2 asymmetric stretching in dimers photogenerated within long-chain diacyl peroxide single crystals. Chem. Phys. Lett. 1986, 130, 259-264.
55. Bernstein, E. R. Site effects in isotopic mixed crystals-site shift, site splitting, orientational effect and intermolecular Fermi resonance in the vibrational spectrum of benzene. J. Chem. Phys. 1969, 50, 4842-4856.
56. Pate, K. L. Probing molecular mobility of reaction-generated carbon dioxide in photolyzed acyl peroxide single crystals: an FT-IR investigation. Ph.D. Thesis, Yale University, New Haven, CT, 2000.
57. Later we discuss at length Mike's extraordinary performance as an undergraduate instructor; he was no slouch at graduate mentoring either. In 1987, he was honored (along with MDH) for the work described in this paragraph with the American Chemical Society's Nobel Laureate Signature Award for Graduate Education in Chemistry.
58. Mills, D. E. Bis(11-bromoundecanoyl) peroxide: remote substituent effects on a solid-state reaction. Ph.D. Thesis, Yale University, New Haven, CT, 1986.
59. Feng, X. W. Mechanistic ESR study in the solid state: radical reactions in crystals of bis(11-bromoundecanoyl) peroxide and its analogs. Ph.D. Thesis, Yale University, New Haven, CT, 1989.
60. Biewer, M. C. Investigation of radical motion in the single-crystal photolytic decomposition mechanism of (11-bromoundecanoyl)(decanoyl) peroxide. Ph.D. Thesis, Yale University, New Haven, CT, 1995.
61. 59
62. Pate, K. L.; McBride, J. M. Using crystal optics to demonstrate single-layer localization of a solid-state chain reaction. Helv. Chim. Acta 2000, 83, 2352-2362.
63. Feng, X. W.; McBride, J. M. Hydrogen atom transfer in photolyzed (S,S)-bis(13-bromo-2-deuteriotridecanoyl) peroxide: control of regiospecificity by crystal chirality. J. Am. Chem. Soc. 1990, 112, 6151-6152.
64. Toscano, J. P., III. The low-temperature photochemistry of nitramine single crystals. Ph.D. Thesis, Yale University, New Haven, CT, 1992.
65. Ryzhkov, L. R.; Toscano, J. P. Crystal lattice effects on the orientation and orbital degeneracy of nitric oxide trapped in nitramine single crystals. Cryst. Growth Des. 2005, 5, 2066-2072.
66. McBride, J. M.; Toscano, J. P. Observation of reaction intermediates in crystalline nitramines. In Proceedings of Workshop on Desensitization of Explosives and Propellants; Rijswijk, Netherlands, 1991.
67. 15N-HNIW. J. Phys. Chem. 1996, 100, 163-169.
68. 2 radical pairs occupying adjacent solvent cavities of α-HNIW, a nitramine hydrate. J. Am. Chem. Soc. 1997, 119, 4826-4833.
69. McBride, J. M.; Bertman, S. B.; Semple, T. C. Structural effects on surfaces within layered crystals. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 4743-4746.
70. McBride, J. M.; Evans, G. T. Steady-state optical spin polarization from a spiropyran at 105 K. Possible evidence for a diradical. Chem. Phys. Lett. 1975, 36, 41-45.
71. Vary, M. W. Part I: Localized nitro n,π* triplets: the triplet states of four nitroindolinobenzopyrans. Part II: EPR studies of radical pairs in crystalline dibenzoyl peroxide. Ph.D. Thesis, Yale University, New Haven, CT, 1979.
72. Vary, M. W.; McBride, J. M. Using spiropyran fragment superposition to assign the EPR spectrum of localized triplet excitation on a distorted aromatic nitro group. Cryst. Growth Des. 2005, 5, 2036-2042.
73. McBride, J. M.; Bertman, S. B.; Cioffi, D. Z.; Segmuller, B. E.; Weber, B. A. Interpreting substituent effects on the crystal packing of long-chain diacyl peroxides: the crystal structures of di(11-bromoundecanoyl) peroxide and di(undecanoyl) peroxide. Mol. Cryst. Liq. Cryst. 1988, 161, 1-24.
74. Bertman, S. B. Solid substituent effects: systematic investigation of the influence of molecular interaction on bulk properties of organic solids. Ph.D. Thesis, Yale University, New Haven, CT, 1990.
75. Swift, J. A.; Pal, R.; McBride, J. M. Using hydrogen-bonds and herringbone packing to design interfaces of 4,4′-disubstituted meso-hydrobenzoin crystals. The importance of recognizing unfavorable packing motifs. J. Am. Chem. Soc. 1998, 120, 96-104.
76. McBride, J. M. Crystal polarity: a window on ice nucleation. Science 1992, 256, 814.
77. Gavish, M.; Wang, J.-L.; Eisenstein, M.; Lahav, M.; Leiserowitz, L. The role of crystal polarity in α-amino acid crystals for induced nucleation of ice. Science 1992, 256, 815-818.
78. Addadi, L.; Berkovitch-Yellin, Z.; Weissbuch, I.; Lahav, M.; Leiserowitz, L. A link between macroscopic phenomena and molecular chirality: Crystals as probes for the direct assignment of absolute configuration of chiral molecules. Top. Stereochem. 1986, 16, 1-85.
79. McBride, J. M.; Bertman, S. B. Using crystal birefringence to study molecular recognition. Angew. Chem., Int. Ed. Engl. 1989, 28, 330-333.
80. See Hollingsworth, M. D. Crystal engineering: from structure to function. Science 2002, 295, 2410-2413 for a brief overview.
81. Tape was often necessary. In no small measure because of Mike's excitement about doing science, his students would often work into the wee hours of the night, long after the machine shops were closed. On Friday afternoons at 4:00 p.m., if there were a few liters of liquid helium left over from a magnet fill, some McBride group student would invariably be in line for it, hoping to spend another Friday night testing Mike's hypotheses on the EPR spectrometer.
82. McBride, J. M. Symmetry reduction in solid solutions: A new method for materials design. Angew Chem., Int. Ed. Engl. 1989, 28, 377-379.
83. Kahr, B.; McBride, J. M. Optically anomalous crystals. Angew. Chem., Int. Ed. Engl. 1992, 31, 1-26.
84. McBride, J. M.; Carter, R. L. Spontaneous resolution by stirred crystallization. Angew. Chem., Int. Ed. Engl. 1991, 30, 293-295.
85. Kondepudi, D. K.; Kaufman, R. J.; Singh, N. Chiral symmetry breaking in sodium chlorate crystallization. Science 1990, 250, 975-977.
86. Swift, J. A. Probing intermolecular interactions: an atomic force microscopy and X-ray investigation of crystal growth and dissolution processes. Ph.D. Thesis, Yale University, New Haven, CT, 1997.
87. These include the Dylan Hixon '88 Prize for Teaching Excellence in the Natural Sciences at Yale College (1992), the DeVane Medal for Distinguished Scholarship and Teaching (1994), and the Yale Science and Engineering Award for Meritorious Service to Yale (1998).
88. Thomas, L. The art of teaching science. New York Times Mag. March 14, 1982; pp 89-92.
89. Berkovitch-Yellin, Z.; Leiserowitz, L. Electron density distribution in cumulenes. Low temperature x-ray study of tetraphenylbutatriene. J. Am. Chem. Soc. 1975, 97, 5627-5628.
90. Berkovitch-Yellin, Z.; Leiserowitz, L. Electron density distribution in cumulenes: an X-ray study of tetraphenylbutatriene at 20°C and -160°C. Acta Crystallogr. 1977, B33, 3657-3669.
91. Chakrabarti, P.; Seiler, P.; Dunitz, J. D.; Schluter, A. D.; Szeimies, G. Experimental evidence for the absence of bonding electron density between inverted carbon atoms. J. Am. Chem. Soc. 1981, 103, 7378-7380.
92. Dunitz, J. D.; Schweizer, W. B.; Seiler, P. X-ray study of the deformation density in tetrafluoroterephthalodinitrile: weak bonding density in the C,F-bond. Helv. Chim. Acta 1983, 66, 123-133.
93. Wiberg, K. B.; Walker, F. H. [1.1.1]Propellane. J. Am. Chem. Soc. 1982, 104, 5239-5240.
94. Groth, P. A. Chemische Krystallographie; Verlag von Wilhelm Engelmann: Leipzig, 1906-1919; Vol. I-V.
95. Wallach, O. Briefwechsel zwischen J. Berzelius und F. Wöhler; Engelmann: Leipzig, 1901; p 291; cited on Chemistry 125 website.
96. Dunitz, J. D.; Harris, K. D. M.; Johnston, R. L.; Kariuki, B. M.; MacLean, E. J.; Psallidas, K.; Schweizer, W. B.; Tykwinski, R. R. New light on an old story: The solid-state transformation of ammonium cyanate into urea. J. Am. Chem. Soc. 1998, 120, 13274-13275.
97. Liebig, J. v.; Wöhler, F. Ann. Phys. Leipzig, Ser. 2 1830, 20, 369. Cited in ref 95.
98. Wöhler, F.; Liebig, J. v. Ann. Pharm. 1832, 3, 249. Cited on the Chemistry 125 website.
99. Skinner, K. J.; Hochster, H. S.; McBride, J. M. o- and p-Semibenzene dimers of benzylic radicals. Autoxidation of quinoid dimers. J. Am. Chem. Soc. 1974, 96, 4301-4306.
100. McBride, J. M. The hexaphenylethane riddle. Tetrahedron 1974, 30, 2009-2022.
101. McBride, J. M. Completion of Koerner's proof that the hydrogens of benzene are homotopic. An application of group theory. J. Am. Chem. Soc. 1980, 102, 4134-4137.
102. This has included Mike's daughter Anne, who is now an Assistant Professor of Biology and Biochemistry at Bowdoin College.
103. Bürgi, H. B.; Dunitz, J. D. From crystal statics to chemical dynamics. Acc. Chem. Res. 1983, 16, 153-161.
104. Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipff, G. Stereochemistry of reaction paths at carbonyl centers. Tetrahedron 1974, 30, 1563-1572.
105. Bürgi, H. B.; Dunitz, J. D.; Shefter, E. Chemical reaction paths. IV. Aspects of O⋯C=O interactions in crystals. Acta Crystallogr. 1974, B30, 1517-1527.
106. McBride, J. M. A rationale for the shape of simple Hückel orbitals. J. Chem. Educ. 1974, 51, 471.
107. Wheeler, L. P. Josiah Willard Gibbs: The History of a Great Mind; Yale University Press: New Haven, 1948; p 141.