{"id":15,"date":"2012-01-20T15:39:35","date_gmt":"2012-01-20T19:39:35","guid":{"rendered":"http:\/\/blogs.vassar.edu\/jotanski\/?page_id=15"},"modified":"2026-05-24T19:13:27","modified_gmt":"2026-05-24T23:13:27","slug":"tanski-research-group","status":"publish","type":"page","link":"https:\/\/pages.vassar.edu\/jotanski\/tanski-research-group\/","title":{"rendered":"Tanski Research Group"},"content":{"rendered":"
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The research being pursued by the Tanski group is generally in the field of transition metal coordination chemistry<\/strong>. Research projects are available for interested students in several fields, including asymmetric catalysis, extended structure coordination chemistry, inorganic medicinal chemistry, and X-ray crystallography.<\/p>\n

Undergraduate students at any level may receive credit or workstudy pay for time spent on research projects. See the bottom of this page for information on students currently working in the Tanski lab.<\/p>\n

<\/a>Major Research Projects: <\/strong><\/h2>\n

1. Gold Coordination Chemistry<\/strong><\/p>\n

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\u201cSynthesis, structural characterization and\u00a0in vitro<\/i>\u00a0anticancer screening of several gold(I) thiolate, dithiocarbonate and dithiocarbamate complexes;\u201d\u00a0Liu, H.<\/u><\/strong>; Tanski, J. M.\u00a0Polyhedron,<\/i>\u00a02022<\/b>, 115999.<\/p>\n<\/div>\n

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2. Small Molecule X-ray Crystallography<\/strong><\/p>\n

Students work with Dr. Tanski, and other faculty members, to determine the crystal and molecular structures of compounds produced in our laboratories here at Vassar – both in coursework and in research – and also those from labs of our collaborators in academia and industry.<\/p>\n

–><\/strong>\u00a0 We are interested in detailed descriptions of molecular structures, including describing different types of intermolecular interactions, such as hydrogen bonding, \u03c0-stacking, halogen-halogen interactions, and C-H\u2022\u2022\u2022X (X = O, N, halogen) interactions.\u00a0 “\u03c0-stacking” should probably be regarded as geometrical arrangement instead of an intermolecular interaction: Some examples:<\/p>\n

\u201cSpectroscopic, crystallographic, and Hirshfeld surface characterization of nine-membered-ring-containing 9-meth\u00adoxy-3,4,5,6-tetra\u00adhydro-1H-benzo[b]azonine-2,7-dione and its parent tetra\u00adhydro\u00adcar\u00adba\u00adzole;\u201d Flores, M. J.; Mai, B.<\/strong>;<\/u>\u00a0Tanski, J. M.\u00a0Acta Cryst.\u00a0<\/em>2023<\/strong>,\u00a0E79<\/em>, 831-836.<\/p>\n

\u201cCrystallographic and spectroscopic characterization of two 1-phenyl-(1H)-imidazoles:4-(1H-imidazol-1-yl)benzaldehyde and 1-(4-methoxyphenyl)-1H-imidazole;\u201d McClements, I. F., Wiesler, C. R.<\/u><\/strong>, \u00a0Tanski, J. M.\u00a0Acta Cryst.\u00a0<\/em>2023<\/strong>,\u00a0E79<\/em>, 678-681.<\/p>\n

\u201c\u03c0-Stacking Motifs in the Crystal Structures of Bis(phosphine) Copper (I) \u03b72<\/sup>-Tetrahydroborate Complexes;\u201d Lueckheide, M.; Rothman, N.; Ko, B.<\/strong>; Tanski, J. M. Polyhedron 2013<\/strong>, 58, 79-84.<\/p>\n

“Analysis of Small Molecule X-ray Crystal Structures: Chemical Crystallography with Undergraduate Students in a Teaching Laboratory;” Aldeborgh, H.; George, K.; Howe, M.; Lowman, H.;\u00a0Moustakas, H.; Strunsky, N.<\/strong>; Tanski, J. M. \u00a0J. Chem. Cryst.\u00a02014<\/strong>, 44, 70-81.<\/p>\n

\u201cCrystal structures of 4-chloropyridine-2-carbonitrile and 6-chloropyridine-2-carbonitrile exhibit different intermolecular \u03c0-stacking, C-H\u00b7\u00b7\u00b7Nnitrile<\/sub> and C-H\u00b7\u00b7\u00b7Npyridine<\/sub> interactions;\u201d Montgomery, M. J., O\u2019Connor, T. J.<\/strong>, Tanski, J. M. Acta Cryst.<\/em>2015<\/strong>, E71<\/em>, 852-856.<\/p>\n

\u201cTwo Achiral Isomers of Chloronitropyridine Crystallize as Polar Materials with Different Molecular Packing Motifs Based on Similar Intermolecular Interactions;\u201d Merritt, H.<\/strong>; Tanski, J. M. J. Chem. Cryst.<\/em> 2018<\/strong>, 48, 109-116.115.<\/p>\n

–><\/strong> \u00a0For details on our analysis of other metrical parameters such as pitch angle, see:<\/p>\n

“Structural Analysis of Bisphenol-A and its Methylene, Sulfur, and Oxygen Bridged Bisphenol AnalogsLim, C. F.; Tanski, J. M.\u00a0J. Chem. Cryst.\u00a02007<\/strong>,\u00a037, 587-595.<\/p>\n

–><\/strong> \u00a0We are also interested in absolute structure, particularly of organic compounds:<\/p>\n

\u201dAza-Crown Macrocycles as Chiral Solvating Agents for Mandelic Acid Derivatives;\u201d Quinn, T. P.; Atwood, P. D.; Tanski, J. M.; Moore, T. F.; Folmer-Andersen, J. F.\u00a0J. Org. Chem.\u00a02011<\/strong>,\u00a076, 10020-10030.<\/p>\n

“Structural Studies of Diaminocyclohexane-Containing Aza-Crown Macrocycles and Their Zn(II) Complexes;”\u00a0Atwood, P. D.;\u00a0Akyant, A.;\u00a0Shalumova, T.;\u00a0Tanski, J. M.;\u00a0Folmer-Andersen, J. F.\u00a0Polyhedron\u00a02014<\/strong>, 67, 191-198.<\/p>\n

\u201cCrystallographic and spectroscopic characterization of (R<\/em>)-O<\/em>-acetylmandelic acid;\u201d Cirbes, C.<\/strong>; Tanski, J. M. Acta Cryst.\u00a0<\/em>2016<\/strong>, E72<\/em>, 901-903.<\/p>\n

Vassar has a Bruker APEX DUO <\/strong>X-ray diffractometer<\/a>.<\/p>\n<\/div>\n

\"Bruker<\/p>\n

3. <\/strong>Asymmetric Lewis Acid Catalysis<\/strong><\/p>\n

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Multiple asymmetric induction in homogeneous catalysis by metal coordination complexes with various different combinations of chiral ligands is an attractive approach to enhancing enantioselectivity in existing catalytic processes. A specific example of such an application is the methylation of aryl aldehydes with dimethyl zinc catalyzed by Lewis acidic metal coordination complexes of chiral alkoxides and a chiral chelating ligand, L*<\/strong>.<\/p>\n<\/div>\n

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In contrast to the more well studied and optimized process of ethylation with diethyl zinc, methylation results in significantly lower enantiomeric excess. We have recently shown that it is possible to modestly increase the enantiomeric excess of 1-phenylethanol obtained from the methylation of benzaldehyde by dichiral double asymmetric induction with a titanium(IV) complex of commercially available BINOL (BINOL = 1,1\u2019-bi-2-naphthol) and the resolved chiral sec-butoxides Ti(OR-2<\/sup>Bu)4<\/sub> or Ti(OS-2<\/sup>Bu)4<\/sub>. (MacMillan, S. N.; Ludford, K. T.; Tanski, J.M. Tetrahedron: Asymmetry<\/em>2008<\/strong> , 19, 543\u2013548.) The simple resolved titanium sec-butoxides, combined with resolved BINOL of the opposite configuration designation, yielded a matched pair that mediates the addition of dimethyl zinc to benzaldehyde(>99% conversion) with higher enantioselectivity (~58%) than resolved BINOL with Ti(Oi<\/sup>Pr)4<\/sub> (~46%) or the mismatched pair (~40%).\u00a0We also investigated another\u00a0chiral chelating ligand, tetrahydrosalen.\u00a0 (MacMillan, S. N.; Jung, C. F.; Shalumova, T.; Tanski, J. M. Inorg. Chim. Acta 2009<\/strong>, 362, 3134-3146.)<\/p>\n

We were later able to achieve even higher enantiomeric excesses of 80-90% using a different chiral diol, R,R<\/em>-TADDOL, although we\u00a0found that the matched pair effect is less prominent with R,R<\/em>-TADDOL than it is with R<\/em>– or S<\/em>-BINOL. We have\u00a0most recetnly observed\u00a0that with modified, chlorinated TADDOL ligands, we can achieve >99% conversion to the methylated product with\u00a096.5% enantiomeric excess.\u00a0 (Baker-Salisbury, M. G.;\u00a0Starkman, B. S.;\u00a0<\/span>Frisenda, G. M.;<\/span>\u00a0Roteta, L. A.; Tanski , J. M. Inorg. Chim. Acta 2014<\/strong>, 409, 394-398.)<\/span><\/p>\n

We have more recently turned our attention to synthesizing chiral substituents on amines by the reduction of imines.<\/strong>\"\"<\/a>\"\"<\/a>\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0URSI 2022<\/strong><\/p>\n<\/div>\n

4. Covalent Metal Organic Networks <\/strong><\/p>\n

Metal-organic coordination network (MOCN) materials formed from rigid organic spacers and metals of known coordination tendencies have become increasingly well studied. Materials with large pores present possibilities for:<\/p>\n