@article {98, title = {Halogen bonding and pi,pi interactions in the solid-state structure of a butadiynylene-linked bis(iodoperfluoroarene)}, journal = {CrystEngComm}, volume = {15}, year = {2013}, month = {2013}, pages = {3097 - 3101}, abstract = {

The solid-state structures of a butadiynylene-linked bidentate halogen bond donor, both as a single component and as a co-crystal with tetra-n-butylammonium iodide, are discussed. Solution-phase binding data indicate that this donor, which possesses only a single degree of conformational freedom, interacts with halides in a 1 : 1 stoichiometry through a convergent binding mode. In contrast, it forms a zigzag-type chain with iodide in the solid state. The X-ray crystallographic data enable detailed studies of the changes in molecular structure and supramolecular organization that accompany the formation of a halogen-bonded network.

}, url = {http://dx.doi.org/10.1039/C2CE26751A}, author = {Walter, Sebastian M. and Sarwar, Mohammed G. and Chudzinski, Michael G. and Herdtweck, Eberhardt and Lough, Alan J. and Huber, Stefan M. and Taylor, Mark S.} } @article {96, title = {Halogen bonding in solution: thermodynamics and applications}, journal = {Chemical Society Reviews}, volume = {42}, year = {2013}, month = {2013}, pages = {1667 - 1680}, abstract = {

Halogen bonds are noncovalent interactions in which covalently bound halogens act as electrophilic species. The utility of halogen bonding for controlling self-assembly in the solid state is evident from a broad spectrum of applications in crystal engineering and materials science. Until recently, it has been less clear whether, and to what extent, halogen bonding could be employed to influence conformation, binding or reactivity in the solution phase. This tutorial review summarizes and interprets solution-phase thermodynamic data for halogen bonding interactions obtained over the past six decades and highlights emerging applications in molecular recognition, medicinal chemistry and catalysis.

}, isbn = {0306-0012}, url = {http://dx.doi.org/10.1039/C2CS35213C}, author = {Beale, Thomas M. and Chudzinski, Michael G. and Sarwar, Mohammed G. and Taylor, Mark S.} } @article {105, title = {Structure and energetics of gas phase halogen-bonding in mono-, bi-, and tri-dentate anion receptors as studied by BIRD}, journal = {Physical Chemistry Chemical Physics}, volume = {15}, year = {2013}, month = {2013}, pages = {7638 - 7647}, abstract = {

Complexes of mono-, bi- (RB), and tridentate (RT) receptors with a range of anions (Cl-, Br-, I-, NO3-, H2PO4-, HSO4-, and tosylate (TsO-)) have been studied in the gas phase by both experimental and theoretical methods. Temperature dependent blackbody infrared radiative dissociation (BIRD) experiments were performed on complexes of C8F17I with Br- and I-, RB with I-, NO3-, HSO4-, H2PO4-, and TsO-, and RT with I-, HSO4- and TsO- and the observed Arrhenius parameters are reported here. Master equation modeling of the BIRD kinetics data was carried out to determine threshold dissociation energies. Geometry optimizations and thermochemistry calculations were performed using the B3LYP/6-31+G(d,p) level of theory. Additional single point energies were calculated using MP2/6-311++G(2d,p). Results were examined in terms of the binding order of various anions as well as the added binding strength from additional halogen bonding (XB) interactions. The relative binding energies of ions were generally consistent with the ordering previously reported from solution phase experiments; however, the relatively strong binding of H2PO4- to the bidentate recepor contrasted the solution phase observation of oxoanions having weaker interactions when compared to halides. An increase in the energy required to remove the same anion from the tridentate receptor when compared to the bidentate and monodentate receptors is explained as being due to the increase in halogen bonding interactions. The possibility of mixed halogen and hydrogen bonded complexes were considered.

}, isbn = {1463-9076}, url = {http://dx.doi.org/10.1039/C3CP00105A}, author = {Gillis, Elizabeth A. L. and Demireva, Maria and Sarwar, Mohammed G. and Chudzinski, Michael G. and Taylor, Mark S. and Williams, Evan R. and Fridgen, Travis D.} } @article {80, title = {Correlations between Computation and Experimental Thermodynamics of Halogen Bonding}, journal = {The Journal of Organic Chemistry}, volume = {77}, year = {2012}, month = {2012/04/06}, pages = {3483 - 3491}, isbn = {0022-3263}, url = {http://dx.doi.org/10.1021/jo300279m}, author = {Chudzinski, Michael G. and Taylor, Mark S.} } @article {82, title = {Anion Receptors Composed of Hydrogen- and Halogen-Bond Donor Groups: Modulating Selectivity With Combinations of Distinct Noncovalent Interactions}, journal = {Journal of the American Chemical Society}, volume = {133}, year = {2011}, month = {2011/07/13}, pages = {10559 - 10567}, isbn = {0002-7863}, url = {http://pubs.acs.org/doi/abs/10.1021/ja202096f}, author = {Chudzinski, Michael G. and McClary, Corey A. and Taylor, Mark S.} } @article {108, title = {Borinic Acids: A Neglected Class of Organoboron Compounds for Recognition of Diols in Aqueous Solution}, journal = {Australian Journal of Chemistry}, volume = {64}, year = {2011}, month = {2011}, pages = {1466 - 1469}, abstract = {

Association constants between diphenylborinic acid and representative analytes capable of reversible two-point covalent binding (diols, catechols, and hydroxy acids) were determined using an indicator-displacement assay. Unlike boronic acids, which have been studied in great detail as receptors for diols and related compounds, borinic acids have effectively been ignored as candidates for such applications. The results of this study indicate that diphenylborinic acid displays high affinity for certain analytes of this type in aqueous solution. Of particular interest are differences between the selectivity of the borinic acid and that of a boronic acid of similar pKa towards the series of analytes studied: the borinic acid displays an unusually high level of discrimination for catechols over carbohydrates. The distinct selectivity observed, and the unique opportunities for steric and electronic tuning of diarylborinic acids, suggest that these compounds hold significant potential for applications in aqueous-phase molecular recognition.

}, url = {http://dx.doi.org/10.1071/CH11294}, author = {Chudzinski, Michael G. and Chi, Yuechuan and Taylor, Mark S.} } @article {109, title = {Carbon{\textendash}carbon bond-forming reactions of α-carbonyl carbocations: exploration of a reversed-polarity equivalent of enolate chemistry}, journal = {Tetrahedron}, volume = {67}, year = {2011}, month = {2011/9/30/}, pages = {7586 - 7592}, abstract = {

Carbon{\textendash}carbon bond-forming reactions of putative α-carbonyl carbocation intermediates generated by Lewis acid- or silver-promoted ionizations of toluenesulfonate or halide leaving groups are described. This under-exploited mode of reactivity represents an {\textquoteleft}umpolung{\textquoteright} of conventional enolate chemistry, and enables C{\textendash}C bond construction in both intra- and intermolecular contexts. Attempts to develop diastereoselective variants of this process using chiral ester and oxazolidinone-based auxiliaries are discussed.

}, keywords = {Allylation, Carbocations, Friedel{\textendash}Crafts reaction, Lactams, Umpolung reactivity}, isbn = {0040-4020}, url = {http://www.sciencedirect.com/science/article/pii/S0040402011011148}, author = {Lai, Ping-Shan and Dubland, Joshua A. and Sarwar, Mohammed G. and Chudzinski, Michael G. and Taylor, Mark S.} } @article {85, title = {N,N'-Diarylsquaramides: General, High-Yielding Synthesis and Applications in Colorimetric Anion Sensing}, journal = {The Journal of Organic Chemistry}, volume = {75}, year = {2010}, month = {2010/06/18}, pages = {3983 - 3992}, isbn = {0022-3263}, url = {http://dx.doi.org/10.1021/jo100104g}, author = {Rostami, Ali and Colin, Alexis and Li, Xiao Yu and Chudzinski, Michael G. and Lough, Alan J. and Taylor, Mark S.} }