Emeritus Professor Stephen Glover

Emeritus Professor - School of Science and Technology

Biography

Steve Glover was educated at Grey High School and then the University of Port Elizabeth, South Africa where he obtained his B.Sc. (1971) majoring in Chemistry and Physics and B.Sc. Hons. (1972) and M.Sc. (1973) degrees in Organic Chemistry. He obtained his Ph.D. from the University of Port Elizabeth in 1976 for his research into reactions and properties of amidyl free radicals. He undertook postdoctoral studies in organotellurium chemistry with the late Professor Sir Derek Barton FRS at The Imperial College of Science and Technology, London for which he was awarded a D.I.C. in 1977, before taking up a lectureship at the University of Port Elizabeth. In 1985, he took up a position at the University of New England where he is currently an Adjunct Professor. His research interests span the areas of physical, biological, and computational organic chemistry and he has over 160 scientific and conference papers. He also has a strong interest in modern approaches to teaching organic chemistry, which he has published in the chemical education literature and has presented at international chemical education symposia. In 1997, he was awarded the University of New England Vice-Chancellor's Award for Excellence in Teaching. He is a Fellow of the Royal Australian Chemical Institute.

Qualifications

MSc, PhD (Port Elizabeth), DIC (Imperial College), CChem, FRACI

Primary Research Area/s

Biological organic chemistry relating to chemical mutagenicity of the unusual amides, N-acyloxy-N-alkoxyamides, -carbamates and -ureas; Physical organic chemistry of anomeric amides, a new class of amides bearing two electronegative atoms at nitrogen; Reaction mechanisms and in particular the HERON reaction discovered by our group at University of New England; Computational chemistry associated with many aspects of structure and reactivity (particularly theoretical properties of amides and -lactams).; Studies of properties of reactive intermediates (free radicals, nitrenium ions, oxenium ions, carbenes, nitrenes, as well as unusual molecules

Research Interests

Biological organic chemistry relating to chemical mutagenicity of the unusual amides, N-acyloxy-N-alkoxyamides, -carbamates and -ureas
Physical organic chemistry of anomeric amides, a new class of amides bearing two electronegative atoms at nitrogen
Reaction mechanisms and in particular the HERON reaction discovered by our group at University of New England
Computational chemistry associated with many aspects of structure and reactivity
Studies of properties of reactive intermediates (free radicals, nitrenium ions, oxenium ions, carbenes, nitrenes, as well as unusual molecules

Publications

[1] Glover, S. A.; Rosser, A. A., Modification of Amidic Resonance Through Heteroatom Substitution at Nitrogen: Anomeric Amides. In Amide Bond Activation, 1 ed.; (Ed. Szostak, M.) 2023, pp 29-77, (Wiley-VCH GmbH:

[2] Glover, S. A., Mutagenicity of N-acyloxy-N-alkoxyamides - QSAR determination of factors controlling activity. Australian Journal of Chemistry 2023;76: 1-24. (10.1071/CH22205)

[3] Glover, S. A.; Schumacher, R. R., Mutagenicity of N-acyloxy-N-alkoxyamides as an indicator of DNA intercalation: The role of fluorene and fluorenone substituents as DNA intercalators. Mutation Research - Genetic Toxicology and Environmental Mutagenesis 2021;863-864: 1-13. (10.1016/j.mrgentox.2020.503299)

[4] Glover, S. A., Comment on "Penicillin's catalytic mechanism revealed by inelastic neutrons and quantum chemical theory" by Z. Mucsi, G. A. Chass, P. Abranyi-Balogh, B. Jojart, D.-C. Fang, A. J. Ramirez-Cuesta, B. Viskolczc and I. G. Csizmadia, Phys. Chem. Chem. Phys., 2013, 15, 20447. Physical Chemistry Chemical Physics 2019;21: 18012-18025. (10.1039/c8cp02413h)

[5] Glover, S. A.; Rosser, A. A., Heteroatom Substitution at Amide Nitrogen-Resonance Reduction and HERON Reactions of Anomeric Amides. Molecules 2018;23: 1-39. (10.3390/molecules23112834)

[6] Greatrex, B.; Meisner, J.; Glover, S.; Raverty, W., Support for a Dioxyallyl Cation in the Mechanism Leading to (−)-Levoglucosenone. The Journal of Organic Chemistry 2017;82: 12294-12299. (10.1021/acs.joc.7b02109)

[7] Glover, S., Development of the HERON Reaction: A Historical Account. Australian Journal of Chemistry 2017;70: 344-361. (10.1071/ch16683)

[8] Glover, S.; Schumacher, R. R., The effect of hydrophobicity upon the direct mutagenicity of N-acyloxy-N-alkoxyamides - bilinear dependence upon LogP. Mutation Research: Genetic Toxicology and Environmental Mutagens 2016;795: 41-50. (10.1016/j.mrgentox.2015.11.005)

[9] Glover, S.; Rosser, A. A., The role of substituents in the HERON reaction of anomeric amides. Canadian Journal of Chemistry 2016;94: 1169-1180. (10.1139/cjc-2016-0300)

[10] Banks, T.; Clay, S.; Glover, S.; Schumacher, R. R., Mutagenicity of N-acyloxy-N-alkoxyamides as an indicator of DNA intercalation part 1: evidence for naphthalene as a DNA intercalator. Organic & Biomolecular Chemistry 2016;14: 3699-3714. (10.1039/c6ob00162a)

[11] Stockton, K.; Glover, S.; Greatrex, B., Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates. Synlett 2015;26: 111-115. (10.1055/s-0034-1379490)

[12] Glover, S.; Rosser, A. A., HERON reactions of anomeric amides: understanding the driving force. Journal of Physical Organic Chemistry 2015;28: 215-222. (10.1002/poc.3322)

[13] Glover, S.; Rosser, A. A.; Taherpour, A.; Greatrex, B., Formation and HERON reactivity of cyclic 'N,N'-dialkoxyamides. Australian Journal of Chemistry 2014;67: 507-520. (10.1071/CH13557)

[14] Glover, S.; Rosser, A. A.; Spence, R., Studies of the Structure, Amidicity, and Reactivity of N-Chlorohydroxamic Esters and N-Chloro-β,β-dialkylhydrazides: Anomeric Amides with Low Resonance Energies. Australian Journal of Chemistry 2014;67: 1344-1352. (10.1071/CH14270)

[15] Schumacher, R. R.; Glover, S.; Gunter, M. Structural effects upon the mutagenicity of N-acyloxy-N-alkoxyamides. 2012.

[16] Glover, S.; Rosser, A. A., Reliable Determination of Amidicity in Acyclic Amides and Lactams. The Journal of Organic Chemistry 2012;77: 5492-5502. (10.1021/jo300347k)

[17] Glover, S.; White, J. M.; Rosser, A. A.; Digianantonio, K. M., Structures of N,N-Dialkoxyamides: Pyramidal Anomeric Amides with Low Amidicity. The Journal of Organic Chemistry 2011;76: 9757-9763. (10.1021/jo201856u)

[18] Glover, S.; Schumacher, R. R.; Bonin, A. M.; Fransson, L. E., Steric effects on the direct mutagenicity of N-acyloxy-N-alkoxyamides - Probes for drug-DNA interactions. Mutation Research: Genetic Toxicology and Environmental Mutagens 2011;722: 32-38. (10.1016/j.mrgentox.2011.02.007)

[19] Glover, S.; Adams, M., Reaction of N-Acyloxy-N-alkoxyamides with Biological Thiol Groups. Australian Journal of Chemistry 2011;64: 443-453. (10.1071/CH10470)

[20] Digianantonio, K. M.; Glover, S.; Johns, J.; Rosser, A. A., Synthesis and thermal decomposition of N,N-dialkoxyamides. Organic & Biomolecular Chemistry 2011;9: 4116-4126. (10.1039/c1ob00008j)

[21] Betz, R.; McCleland, C.; Glover, S., 2-(4-Iodophenoxy)acetamide. Acta crystallographica. Section E 2011;67: 1-11. (10.1107/S1600536811025840)

[22] Johns, J. P.; van Losenoord, A.; Mary, C.; Garcia, P.; Pankhurst, D.; Rosser, A. A.; Glover, S., Thermal Decomposition of N-Acyloxy-N-alkoxyamides: a New HERON Reaction. Australian Journal of Chemistry 2010;63: 1717-1729. (10.1071/CH10350)

[23] Hine, B. C.; Hunt, P. W.; Beasley, A. M.; Windon, R. G.; Glover, S. A.; Colditz, I. G., Selective transport of IgE into ovine mammary secretions. Research in Veterinary Science 2010;89: 184-190.

[24] Chakraborty, M.; Jin, K. J.; Glover, S.; Novak, M., Characterization of 4-(Benzothiazol-2-yl)phenylnitrenium Ion from a Putative Metabolite of a Model Antitumor Drug. The Journal of Organic Chemistry 2010;75: 5296-5304. (10.1021/jo101275y)

[25] Wang, Y.-T.; Jin, K. J.; Myers, L. R.; Glover, S.; Novak, M., Hydrolysis and Photolysis of 4-Acetoxy-4-(benzothiazol-2-yl)-2,5-cyclohexadien-1-one, a Model Anti-Tumor Quinol Ester. The Journal of Organic Chemistry 2009;74: 4463-4471.

[26] Glover, S. A., N-Heteroatom-substituted hydroxamic esters. In The Chemistry of Hydroxylamines, Oximes and Hydroxamic, Acids, Part 2, (Eds. Rappoport, Z.; Liebman, J. F.) 2009, pp 839-923, (Wiley: Chichester).

[27] Craig, T.; Grave, P.; Glover, S., HPLC-MS characterisation of adsorbed residues from Early Iron Age ceramics, Gordion, Central Anatolia. In New Directions in Archaeological Science, 2009, pp 203-212, (ANU Press:

[28] Cavanagh, K. L.; Glover, S.; Price, H.; Schumacher, R. R., S'N'2 Substitution Reactions at the Amide Nitrogen in the Anomeric Mutagens, 'N-Acyloxy-N-alkoxyamides'. Australian Journal of Chemistry 2009;62: 700-710. (10.1071/CH09166)

[29] Wang, Y.-T.; Jin, K. J.; Leopold, S. H.; Wang, J.; Peng, H.-L.; Platz, M. S.; Xue, J.; Phillips, D. L.; Glover, S.; Novak, M., Characterisation of Reactive Intermediates Generated During Photolysis of 4-Acetoxy-4-aryl2,5-cyclohexadienones: Oxenium lons and Aryloxy Radicals. Journal of the American Chemical Society 2008;130: 16021-16030. (10.1021/ja805336d)

[30] Hine, B. C.; Glover, S.; Colditz, I. Plasmablast Recruitment to the Ruminant Mammary Gland. 2008.

[31] Glover, S. A., N-Acyloxy-N-alkoxyamide — Structure, Properties, Reactivity and Biological Activity. In Adv. Phys. Org. Chem., (Ed. Richard, J.) 2008, Vol. 42, pp 35-123, (Elsevier: London).

[32] Novak, M.; Brinster, A. M.; Dickhoff, J. N.; Erb, J. M.; Jones, M. P.; Leopold, S. H.; Vollman, A. T.; Wang, Y.-T.; Glover, S., Chemistry of 4-alkylaryloxenium ion "precursors": Sound and fury signifying something? The Journal of Organic Chemistry 2007;72: 9954-9962. (10.1021/jo701853e)

[33] Hauptli, S. L.; Colegate, S. M.; Glover, S. A.; McClure, S. J., Dose Response of Tunicamycins in Sheep Following Intra-duodenal Administration. In Poisonous Plants Global Research and Solutions, (Eds. Panter, K. E.; Wierenga, T. L.; Pfister, J. A.) 2007, pp 242-247, (CABI Publishing: Cambridge, MA).

[34] Glover, S., Truly Australian: the HERON reaction. Chemistry in Australia 2007;74: 6-10.

[35] Glover, S., N-Acyloxy-N-alkoxyamides - structure, properties, reactivity and biological activity. Advances in Physical Organic Chemistry 2007;42: 35-123. (10.1016/S0065-3160(07)42002-0)

[36] Novak, M.; Poturalski, M. J.; Johnson, W. L.; Jones, M. P.; Wang, Y.; Glover, S., 4'-substituted-4-biphenylyloxenium ions: reactivity and selectivity in aqueous solution. The Journal of Organic Chemistry 2006;71: 3778-3785. (10.1021/jo060198r)

[37] Glover, S., HERON rearrangement (Heteroatom Rearrangements on Nitrogen). 14 ed.; Merck Research Laboratories, Merck & Co, Inc: 2006; Vol. 1, pp ONR-43-ONR-43.

[38] Glover, S., Molecular Orbital Properties as an Aid to Teaching Undergraduate Organic Chemistry. The Chemical Educator 2006;11: 77-83. (10.1333/s00897061017a)

[39] Andrews, L.; Bonin, A. M.; Fransson, L. E.; Gillson, A.; Glover, S., The Role of Steric Effects in the Direct Mutagenicity of N-acyloxy-N-alkoxyamides. Mutation Research: Genetic Toxicology and Environmental Mutagens 2006;605: 51-62. (10.1016/j.mrgentox.2006.02.003)

[40] Novak, M.; Glover, S., The Hydrolysis of 4-acyloxy-4-substituted-2,5-cyclohexadienones: Limitations of Aryloxenium Ion Chemistry. Journal of the American Chemical Society 2005;127: 8090-8097. (10.1021/ja050899q)

[41] Hine, B. C.; Colditz, I.; Hunt, P. W.; Glover, S. In Plasmablast recruitment to the ruminant mammary gland, Wiley-Blackwell Munksgaard: 2005; pp 442-442.

[42] Glover, S.; Rauk, A.; Buccigross, J. M.; Campbell, J. J.; Hammond, G. P.; Mo, G.; Andrews, L.; Gillson, A., The HERON Reaction: Origin, theoretical background, and prevalence. Canadian Journal of Chemistry 2005;83: 1492-1509. (10.1139/V05-150)

[43] Glover, S.; Novak, M., Computational studies of the properties of phenyloxenium ions: A comparison with phenylnitrenium and phenylcarbenium ions. Canadian Journal of Chemistry 2005;83: 1372-1381. (10.1139/v05-149)

[44] Novak, M.; Glover, S., Generation and Trapping of the 4-Biphenylyloxenium Ion by Water and Azide: Comparison with the 4-Biphenylylnitrenium Ion. Journal of the American Chemical Society 2004;126: 7748-7749. (10.1021/ja047488e)

[45] Andrews, L.; Banks, T.; Bonin, A. M.; Clay, S.; Gillson, A.-M.; Glover, S., Mutagenic N-Acyloxy-N-alkoxyamides: Probes for Drug-DNA Interactions. Australian Journal of Chemistry 2004;57: 377-381. (10.1071/CH03276)

[46] Gillson, A.-M.; Glover, S.; Tucker, D.; Turner, P., Crystal structures and properties of mutagenic 'N'-acyloxy-'N'-alkoxyamides - 'most pyramidal' acyclic amides. Organic & Biomolecular Chemistry 2003;1: 3430-3437. (10.1039/b306098p)

[47] Banks, T.; Bonin, A.; Glover, S.; Prakash, A., Mutagenicity and DNA damage studies of N-acyloxy-N-alkoxyamides: the role of electrophilic nitrogen. Organic & Biomolecular Chemistry 2003;1: 2238-2246. (10.1039/b301618h)

[48] Mo, G.; Glover, S., Hindered ester formation by Sɴ2 azidation of N-acetoxy-N-alkoxyamides and N-alkoxy-N-chloroamides - novel application of HERON rearrangements. Journal of the Royal Chemical Society: Perkin Transactions 2 2002: 1728-1739. (10.1039/B111250N)

[49] Glover, S.; Rauk, A., A computational investigation of the structure of the novel anomeric amide N-azido-N-methoxyformamide and its concerted decomposition to methyl formate and nitrogen. Journal of the Royal Chemical Society: Perkin Transactions 2 2002: 1740-1746. (10.1039/B204232K)

[50] Glover, S., SN2 reactions at amide nitrogen - theoretical models for reactions of mutagenic N-acyloxy-N-alkoxyamides with bionucleophiles. ARKIVOC 2001;2: 143-160.

Memberships