A comparison of the structure and bonding in the aliphatic boronic R–B(OH)2 and borinic R–BH(OH) acids (R=H; NH2, OH, and F): a computational investigation

[1]  Joseph D. Larkin,et al.  A computational investigation of monosubstituted boroxines(RH2B3O3): structure and formation , 2015, Structural Chemistry.

[2]  A. Gordon,et al.  On the multiple BO bonding using the topological analysis of Electron Localisation Function (ELF) , 2015 .

[3]  K. Abboud,et al.  Boronic Acid-Based Hydrogels Undergo Self-Healing at Neutral and Acidic pH. , 2015, ACS macro letters.

[4]  Y. Miyahara,et al.  Current Development Status and Perspectives of Self-Regulated Insulin Delivery Systems: A Review , 2014 .

[5]  P. Skládal,et al.  Boronic acids for sensing and other applications - a mini-review of papers published in 2013 , 2014, Chemistry Central Journal.

[6]  J. Sun,et al.  Boronic acid-based enzyme inhibitors: a review of recent progress. , 2014, Current medicinal chemistry.

[7]  T. Weil,et al.  Reversible click reactions with boronic acids to build supramolecular architectures in water. , 2014, Chemistry, an Asian journal.

[8]  Ning Xia,et al.  Boronic Acid-Based Approach for Separation and Immobilization of Glycoproteins and Its Application in Sensing , 2013, International journal of molecular sciences.

[9]  Yongjun Zhang,et al.  Boronic acid-containing hydrogels: synthesis and their applications. , 2013, Chemical Society reviews.

[10]  Mark S. Taylor,et al.  Regioselective silylation of pyranosides using a boronic acid/Lewis base co-catalyst system. , 2013, Organic & biomolecular chemistry.

[11]  Mark S. Taylor,et al.  9-Hetero-10-boraanthracene-derived borinic acidcatalysts for regioselective activation of polyols , 2013 .

[12]  J. Vasseur,et al.  Boron and nucleic acid chemistries: merging the best of both worlds. , 2013, Chemical Society reviews.

[13]  F. Marken,et al.  Exploiting the reversible covalent bonding of boronic acids: recognition, sensing, and assembly. , 2013, Accounts of chemical research.

[14]  Byron E. Collins,et al.  On the rate of boronate ester formation in ortho-aminomethyl-functionalised phenyl boronic acids , 2013, Supramolecular chemistry.

[15]  F. Marken,et al.  The development of boronic acids as sensors and separation tools. , 2012, Chemical record.

[16]  H. Fang,et al.  The progress of selective fluorescent chemosensors by boronic acid. , 2012, Current medicinal chemistry.

[17]  Zhiqian Guo,et al.  Recognition and sensing of various species using boronic acid derivatives. , 2012, Chemical communications.

[18]  Mark S. Taylor,et al.  Regioselective, borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: expansion of substrate scope and mechanistic studies. , 2012, Journal of the American Chemical Society.

[19]  V. Dembitsky,et al.  Boron containing compounds as protease inhibitors. , 2012, Chemical reviews.

[20]  R. Scorei.  Is Boron a Prebiotic Element? A Mini-review of the Essentiality of Boron for the Appearance of Life on Earth , 2012, Origins of Life and Evolution of Biospheres.

[21]  Joseph D. Larkin,et al.  Heats of Formation for the Boronic Acids R-B(OH)2 and Boroxines R3B3O3 (R=H, Li, HBe, H2B, H3C, H2N, HO, F, and Cl) Calculated at the G2, G3, and G4 Levels of Theory. , 2012, Computational & theoretical chemistry.

[22]  R. Saini,et al.  Multifunctional Boronic Acid Crosslinker for Fracturing Fluids , 2012 .

[23]  M. Chudziński,et al.  Borinic Acids: A Neglected Class of Organoboron Compounds for Recognition of Diols in Aqueous Solution , 2011 .

[24]  T. Bein,et al.  Synthesis of well-ordered COF monolayers: surface growth of nanocrystalline precursors versus direct on-surface polycondensation. , 2011, ACS nano.

[25]  B. Sumerlin,et al.  Biomedical applications of boronic acid polymers , 2011 .

[26]  Mark S. Taylor,et al.  Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalyst. , 2011, Journal of the American Chemical Society.

[27]  S. Benkovic,et al.  Boron-containing inhibitors of synthetases. , 2011, Chemical Society reviews.

[28]  K. Bhat,et al.  Thermodynamics of boroxine formation from the aliphatic boronic acid monomers R-B(OH)2 (R = H, H3C, H2N, HO, and F): a computational investigation. , 2011, The journal of physical chemistry. A.

[29]  J. Boucher,et al.  Aminoboronic acids and esters: from synthetic challenges to the discovery of unique classes of enzyme inhibitors. , 2011, Chemical Society reviews.

[30]  Lina Chan,et al.  Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative. , 2011, Organic letters.

[31]  Mark S. Taylor,et al.  Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives. , 2011, Journal of the American Chemical Society.

[32]  T. James,et al.  Boronic acid building blocks: tools for sensing and separation. , 2011, Chemical communications.

[33]  T. James,et al.  Boronic acid building blocks: tools for self assembly. , 2011, Chemical communications.

[34]  T. James,et al.  Boron based anion receptors as sensors. , 2010, Chemical Society reviews.

[35]  C. Mcguigan,et al.  Boronic acids in medicinal chemistry: anticancer, antibacterial and antiviral applications , 2010 .

[36]  S. Shinkai,et al.  Artificial Receptors as Chemosensors for Carbohydrates , 2010 .

[37]  P. Iovine,et al.  Boroxine chemistry and applications: A perspective. , 2010, Dalton transactions.

[38]  Steven E. Wheeler,et al.  A hierarchy of homodesmotic reactions for thermochemistry. , 2009, Journal of the American Chemical Society.

[39]  B. Brooks,et al.  A computational characterization of boron-oxygen multiple bonding in HN=CH-CH=CH-NH-BO. , 2008, The journal of physical chemistry. A.

[40]  S. Shinkai,et al.  Boronic acids in molecular self-assembly. , 2008, Chemistry, an Asian journal.

[41]  I. Pashalidis,et al.  A computational study of the conformations of the boric acid (B(OH)3), its conjugate base ((HO)2BO-) and borate anion (B(OH)4-) , 2008 .

[42]  G. Żukowska,et al.  Structural and spectroscopic properties of an aliphatic boronic acid studied by combination of experimental and theoretical methods. , 2008, The Journal of chemical physics.

[43]  N. Petasis.  Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry , 2007 .

[44]  B. Brooks,et al.  A computational investigation of the geometrical structure and protodeboronation of boroglycine, H2N-CH2-B(OH)2. , 2007, The journal of physical chemistry. A.

[45]  S. Benkovic,et al.  Identification of a novel boron-containing antibacterial agent (AN0128) with anti-inflammatory activity, for the potential treatment of cutaneous diseases. , 2006, Bioorganic & medicinal chemistry letters.

[46]  S. Shinkai,et al.  Boronic Acids in Saccharide Recognition , 2006 .

[47]  B. Brooks,et al.  Structure of the boronic acid dimer and the relative stabilities of its conformers. , 2006, The journal of physical chemistry. A.

[48]  A. Cowley,et al.  Synthesis and characterization of a coordinated oxoborane: Lewis acid stabilization of a boron-oxygen double bond. , 2005, Journal of the American Chemical Society.

[49]  A. Perrin,et al.  Ground-state constants, ab initio anharmonic force field, and equilibrium structure of F2BOH , 2004 .

[50]  V. Dembitsky,et al.  Recent advances in the medicinal chemistry of alpha-aminoboronic acids, amine-carboxyboranes and their derivatives. , 2004, Mini reviews in medicinal chemistry.

[51]  M. L. Bell,et al.  Modular fluorescence sensors for saccharides. , 2002, Chemical communications.

[52]  Thomas F. Koetzle,et al.  Study of the N−H···H−B Dihydrogen Bond Including the Crystal Structure of BH3NH3 by Neutron Diffraction , 1999 .

[53]  D. Linder,et al.  Structures and thermochemistry of BHlFm(OH)n and several XYBO compounds at the G-2 level of theory , 1999 .

[54]  V. Nevalainen.  HB(OH)2 and H2CO as probes for a study on binding of dialkoxyboranes and ketones to oxazaborolidines capable of catalyzing the enantioselective reduction of ketones , 1996 .

[55]  D. K. Straub.  Lewis Structures of Boron Compounds Involving Multiple Bonding , 1995 .

[56]  Kirk A. Peterson,et al.  Benchmark calculations with correlated molecular wave functions. IV. The classical barrier height of the H+H2→H2+H reaction , 1994 .

[57]  J. Cioslowski,et al.  A new robust algorithm for fully automated determination of attractor interaction lines in molecules , 1994 .

[58]  G. Leroy,et al.  Evaluation of the bond energy terms for the various types of boron-nitrogen bonds , 1993 .

[59]  M. Sugie,et al.  Microwave Spectroscopic Detection of Fluoroborane, BH2F , 1993 .

[60]  Angela K. Wilson,et al.  Gaussian basis sets for use in correlated molecular calculations. IX. The atoms gallium through krypton , 1993 .

[61]  J. B. Jones,et al.  Borinic acid inhibitors as probes of the factors involved in binding at the active sites of subtilisin carlsberg and α-chymotrypsin , 1992 .

[62]  B. Ault,et al.  Matrix isolation study of the mechanism of the reaction of diborane with ammonia : pyrolysis of the H3B.NH3 adduct , 1992 .

[63]  T. Dunning,et al.  Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions , 1992 .

[64]  Jerzy Cioslowski,et al.  Covalent bond orders in the topological theory of atoms in molecules , 1991 .

[65]  J. V. Ortiz.  An electron propagator study of bonding in aminoborane , 1989 .

[66]  C. D. Esposti,et al.  The millimeter and submillimeter-wave spectrum of boron monofluoride: equilibrium structure , 1989 .

[67]  T. H. Dunning.  Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen , 1989 .

[68]  L. Curtiss,et al.  Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint , 1988 .

[69]  John E. Carpenter,et al.  Analysis of the geometry of the hydroxymethyl radical by the “different hybrids for different spins” natural bond orbital procedure , 1988 .

[70]  M. Sugie,et al.  Microwave spectrum and molecular structure of aminoborane, BH2NH2 , 1987 .

[71]  S. Rettrup,et al.  Electron Density of Orthoboric Acid Determined by X-ray Diffraction at 105 K and ab initio Calculations , 1986 .

[72]  A. Cox,et al.  The microwave spectrum and structure of CH3BBr2 , 1986 .

[73]  C. Matsumura,et al.  Microwave spectrum, structure, dipole moment, quadrupole coupling constants, and barrier to internal rotation of methoxyborane, CH3OBH2 , 1986 .

[74]  F. Weinhold,et al.  Natural population analysis , 1985 .

[75]  S. So.  A theoretical study of the conformations of BF(OH)2 , 1982 .

[76]  J. E. Boggs,et al.  Accurate ab initio gradient calculation of the structures and conformations of some boric and fluoroboric acids. Basis-set effects on angles around oxygen , 1981 .

[77]  C. Matsumura,et al.  Microwave spectrum of borinic acid BH2OH , 1981 .

[78]  Frank Weinhold,et al.  Natural hybrid orbitals , 1980 .

[79]  J. E. Boggs,et al.  The barriers to methyl group rotation in s-cis- and s-trans-methyl nitrite , 1980 .

[80]  P. Bailey,et al.  Boron-containing antibacterial agents: effects on growth and morphology of bacteria under various culture conditions , 1980, Antimicrobial Agents and Chemotherapy.

[81]  C. Matsumura,et al.  Microwave spectrum of fluorodihydroxy borane, BF(OH)2 , 1979 .

[82]  C. Matsumura,et al.  Microwave spectroscopic detection of BFHOH and BH(OH)2 , 1978 .

[83]  C. Bock,et al.  Homodesmotic reactions for the assessment of stabilization energies in benzenoid and other conjugated cyclic hydrocarbons , 1976 .

[84]  C. Bock,et al.  An alternative approach to the problem of assessing stabilization energies in cyclic conjugated hydrocarbons , 1975 .

[85]  J. Pople,et al.  Molecular orbital theory of the electron structure of organic compounds. XXIV. Geometries and energies of small boron compounds. Comparisons with carbocations , 1975 .

[86]  H. Seip,et al.  Barrier to internal rotation and π-bonding in mercaptoborane, H2BSH, studied by ab initio calculations , 1974 .

[87]  R. Curl,et al.  Microwave Spectrum of BF2OH , 1972 .

[88]  Henry A. Bent,et al.  An Appraisal of Valence-bond Structures and Hybridization in Compounds of the First-row elements. , 1961 .

[89]  M. Plesset,et al.  Note on an Approximation Treatment for Many-Electron Systems , 1934 .

[90]  A. Gordon,et al.  On the multiple B–N bonding in boron compounds using the topological analysis of electron localization function (ELF) , 2011 .

[91]  Giovanni Scalmani,et al.  Gaussian 09W, revision A. 02 , 2009 .

[92]  Y. Endo,et al.  Microwave spectrum, molecular structure, and force field of HBO , 1989 .

[93]  R. Suenram,et al.  Microwave spectrum, torsional barrier, and structure of BH3NH3 , 1983 .

[94]  C. Bock,et al.  An alternative approach to the problem of assessing destabilization energies (strain energies) in cyclic hydrocarbons , 1976 .