Supramolecular Aggregation in Alkaline Earth Metal Amino Benzoates with 1,10‐Phenanthroline AuxiliaryFootnote

Dedicated to Professor Herbert W. Roesky for his outstanding contributions to chemistry.

This work was financially supported by DST and CSIR, New Delhi. R.M. thanks DST for a Swarnajayanti Fellowship and R. K. thanks CSIR for a Senior Research Fellowship.

References

• Wiklund , P. and Bergman , J. 2004 . Alkylation and acylation of basic salts of anthranilic acid . Tetrahedron Lett. , 45 : 969 – 972 .
   Web of Science ®Google Scholar
• Kamnev , A. A. , Kuzmann , E. , Perfiliev , Y. D. , Vako , G. and Vertes , A. 1999 . Mossbauer and FTIR spectroscopic studies of iron anthranilates: coordination, structure and some ecological aspects of iron complexation . J. Mol. Struct. , 482–483 : 703 – 711 .
   Web of Science ®Google Scholar
• Forbes , R. T. , York , P. and Davidson , J. R. 1995 . Dissolution kinetics and solubilities of p‐aminosalicylic acid and its salts . Int. J. Pharm. , 126 : 199 – 208 .
   Web of Science ®Google Scholar
• Ishida , H. , Singh , M. , Donowaki , K. and Ohkubo , K. 1995 . Highly effective binding of phosphomonoester with neutral cyclic peptides which include a non‐natural amino acid . J. Org. Chem. , 60 : 5374 – 5375 .
   Web of Science ®Google Scholar
• Ishida , H. , Donowaki , K. , Singh , M. and Ohkubo , K. 1995 . Serine proteinases mimics: hydrolytic activity of cyclic peptides which include a non‐natural amino acid . Tetrahedron Lett. , 36 : 8987 – 8990 .
   Web of Science ®Google Scholar
• Kubik , S. and Goddard , R. 1999 . A new cyclic pseudopeptide composed of (L)‐proline and 3‐aminobenzoic acid subunits as a ditopic receptor for the simultaneous complexation of cations and anions . J. Org. Chem. , 64 : 9475 – 9486 .
   Web of Science ®Google Scholar
• Kubik , S. and Goddard , R. 2000 . Intramolecular conformational control in a cyclic peptide composed of alternating l‐proline and substituted 3‐aminobenzoic acid subunits . Chem. Commun. , : 633 – 634 .
   Google Scholar
• Pohl , S. , Goddard , R. and Kubik , S. 2001 . A new cyclic tetrapeptide composed of alternating l‐proline and 3‐aminobenzoic acid subunits . Tetrahedron Lett. , 42 : 7555 – 7558 .
   Web of Science ®Google Scholar
• Dutt , A. , Drew , M. G. B. and Pramanik , A. 2005 . β‐Sheet mediated self‐assembly of dipeptides of ω ‐amino acids and remarkable fibrillation in the solid state . Org. Biomol. Chem. , 3 : 2250 – 2254 .
   PubMed Web of Science ®Google Scholar
• Kundu , S. K. , Mazumdar , P. A. , Das , A. K. , Bertolasi , V. and Pramanik , A. 2002 . Parallel β‐sheet assemblage in a model dipeptide: an X‐ray diffraction study . J. Chem. Soc., Perkin Trans. , 2 : 1602 – 1604 .
   Google Scholar
• Dutt , A. , Drew , M. G. B. and Pramanik , A. 2005 . m‐Aminobenzoic acid inserted β‐turn in acyclic tripeptides: a peptidomimetic design . Tetrahedron , 61 : 11163 – 11167 .
   Web of Science ®Google Scholar
• Mattos , C. , Petsko , G. A. and Karplus , M. 1994 . Analysis of Two‐residue Turns in Proteins . J. Mol. Biol. , 238 : 733 – 747 .
   PubMed Web of Science ®Google Scholar
• Kabsch , W. and Sander , C. 1983 . Dictionary of protein secondary structure: pattern recognition of hydrogen‐bonded and geometrical features . Biopolymers , 22 : 2577 – 2637 .
   PubMed Web of Science ®Google Scholar
• Wilmont , C. M. and Thornton , J. M. 1988 . Analysis and prediction of the different types of β‐turn in proteins . J. Mol. Biol. , 203 : 221 – 232 .
   PubMed Web of Science ®Google Scholar
• Wiesbrock , F. and Schmidbaur , H. 2003 . Complexity of coordinative bonding in thallium(I) anthranilates and salicylates . J. Am. Chem. Soc. , 125 : 3622 – 3630 .
   PubMed Web of Science ®Google Scholar
• Starosta , W. , Ptasiewicz‐Bak , H. and Leciejewicz , J. 2002 . The crystal and molecular structure of a new calcium(ii) complex with pyridine‐2,6‐dicarboxylate, water and nitrate ligands . J. Coord. Chem. , 55 : 1147 – 1153 .
   Web of Science ®Google Scholar
• Starosta , W. , Ptasiewicz‐bak , H. and Leciejewicz , J. 2003 . The crystal structures of two calcium(ii) complexes with pyrazine‐2,6‐dicarboxylate and water ligands . J. Coord. Chem. , 56 : 677 – 682 .
   Web of Science ®Google Scholar
• Hundal , G. , Martin , M.‐R. , Hundal , M. S. and Poonia , N. S. 1996 . Acta Cryst. , C52 : 786 – 789 .
   Google Scholar
• Debuyst , R. , Dejehet , F. , Dekandelaer , M. C. , Declerco , J. P. , Germain , G. and Van Meerssche , M. 1979 . J. Chim. Phys. , 78 : 1117 – 1124 .
   Google Scholar
• Plater , M. J. , Howie , R. A. and Roberts , A. J. 1997 . Hydrothermal synthesis and X‐ray structural characterization of calcium benzene‐1,3,5‐tricarboxylate . Chem. Commun. , : 893 – 894 .
   Web of Science ®Google Scholar
• Plater , M. J. , Roberts , A. J. , Marr , J. , Lachowski , E. E. and Howie , R. A. 1998 . Hydrothermal synthesis and characterization of alkaline‐earth metal salts of benzene‐1,3,5‐tricarboxylic acid . J. Chem. Soc., Dalton Trans. , : 797 – 802 .
   Google Scholar
• Zhu , H.‐F. , Zhang , Z.‐H. , Sun , W.‐Y. , Okamura , T.‐A. and Ueyama , N. 2005 . Syntheses, structures, and properties of two‐dimensional alkaline earth metal complexes with flexible tripodal tricarboxylate ligands . Crys. Growth Des. , 5 ( 1 ) : 177 – 182 .
   Web of Science ®Google Scholar
• Lewandowski , W. , Dasiewicz , B. , Koczoń , P. , Skierski , J. , Dobrosz‐Teperek , K. , Świsłocka , R. , Fuks , L. , Priebe , W. and Mazurek , A. P. 2002 . Vibrational study of alkaline earth metal nicotinates, benzoates and salicylates . J. Molecular Str. , 604 : 189 – 193 .
   Web of Science ®Google Scholar
• Deacon , G. B. , Forsyth , M. , Junk , P. C. , Leary , S. G. and Moxey , G. J. 2006 . Synthesis and structural diversity of rare earth anthranilate complexes . Polyhedron , 25 : 379 – 386 .
   Web of Science ®Google Scholar
• Świsłocka , R. , Regulska , E. , Samsonowicz , M. , Hrynaszkiewicz , T. and Lewandowski , W. 2005 . Molecular structure of 3‐aminobenzoic acid complexes with alkali metals . Spectrochim. Acta. Part A , 61 : 2966 – 2973 .
   PubMed Web of Science ®Google Scholar
• Branch , C. S. , Lewinski , J. , Justyniak , I. , Bott , S. G. , Lipkowski , J. and Barron , A. R. 2001 . Aluminium and gallium compounds of salicylic and anthranilic acids: examples of weak intra‐molecular hydrogen bonding . J. Chem. Soc. Dalton Trans. , : 1253 – 1258 .
   Google Scholar
• Murugavel , R. , Karambelkar , V. V. , Anantharaman , G. and Walawalkar , M. G. 2000 . Synthesis, spectral characterization, and structural studies of 2‐aminobenzoate complexes of divalent alkaline earth metal ions: X‐ray crystal structures of [Ca(2‐aba)2(OH2)3]α, [{Sr(2‐aba)2(OH2)2} · H2O]α, and [Ba(2‐aba)2(OH2)]n (2‐abaH=2‐NH2C6H4COOH) . Inorg. Chem. , 39 : 1381 – 1390 .
   PubMed Web of Science ®Google Scholar
• Murugavel , R. , Baheti , K. and Anantharaman , G. 2001 . Reactions of 2‐Mercaptobenzoic acid with divalent alkaline earth metal ions: Synthesis, spectral studies, and single‐crystal X‐ray structures of calcium, strontium, and barium complexes of 2,2′‐dithiobis(benzoic acid) . Inorg. Chem. , 40 : 6870 – 6878 .
   PubMed Web of Science ®Google Scholar
• Fox , S. , Busching , I. , Barklage , W. and Strasdeit , H. 2007 . Coordination of biologically important α‐amino acids to Calcium(II) at high pH: insights from crystal structures of calcium α‐aminocarboxylates . Inorg. Chem. , 46 : 818 – 824 .
   PubMed Web of Science ®Google Scholar
• Hill , A. G. and Curran , C. 1960 . Infrared and ultraviolet absorption spectra of some salts and metal complexes of anthranilic acid . J. Phys. Chem. , 64 : 1519 – 1522 .
   Web of Science ®Google Scholar
• Murugavel , R. and Banerjee , S. 2003 . First alkaline earth metal 3‐aminobenzoate (3‐aba) complex: 1‐D polymeric [Ca(3‐aba)2(H2O)2]n assembly . Inorg. Chem. Commun. , 6 : 810 – 814 .
   Web of Science ®Google Scholar
• Murugavel , R. , Anantharaman , G. , Krishnamurthy , D. , Sathiyendiran , M. and Walawalker , M. G. 2000 . Extended metal‐organic solids based on benzenepolycarboxylic and aminobenzoic acids . Proc. Indian Acad. Sci. , 112 : 273 – 290 .
   Google Scholar
• Cole , L. B. and Holt , E. M. 1989 . Alkali and alkaline earth complexation to derivatives of salicylic acid: [Calcium(p‐aminosalicylate) (acetate) (H2O)](H2O), Magnesium(salicylate)2(H2O)4, Magnesium (p‐aminosalicylate)2(H2O)4, Magnesium(2,6‐pyridinedicarboxylate)‐(H2O)3(H2O)2 and Sodium(p‐aminosalicylate) (H2O)2 . Inorg. Chim. Acta , I60 : 195 – 203 .
   Google Scholar
• Chowdhury , S. R. , Komiyama , T. , Yukawa , Y. and Bhattacharyya , R. 2004 . The first heterobimetallic one dimensional cyano bridged nitrosyl complex containing an alkaline earth metal: synthesis, characterization and crystal structure of the complex [Sr(Phen)2(DMF)2] [Fe(NO)(CN)5] . Inorg. Chem. Commun. , 7 : 1117 – 1119 .
   Web of Science ®Google Scholar
• Datta , A. , Hossain , G. M. G. , Karan , N. K. , Abdul Malik , K. M. and Mitra , S. 2003 . A novel trinuclear cyano‐bridged calcium(II)‐/iron(III) complex; [(phen)2(H2O)2CaNC(NC)4FeCNCa(OH2)(Phen)2NO3] · H2O. Inorg. Chem . Commun. , 6 : 266 – 269 .
   Google Scholar
• Archer , L. , Hampden‐Smith , M. J. and Duesler , E. 1998 . Synthesis, characterization and reactivity of crown ether adducts of barium carboxylates: Ba(O2CCH3)2(18‐crown‐6) · 4H2O and Ba(O2C(CH2)4CO2)(18‐crown‐6) · 8H2O . Polyhedron , 17 ( 5–6 ) : 713 – 723 .
   Web of Science ®Google Scholar
• Arunasalam , V.‐C. , Baxter , I. , Drake , S. R. , Hursthouse , M. B. , Abdul Malik , K. M. and Otway , D. J. 1995 . Synthesis and characterization of the first group 2 mixed β‐diketonate alkoxide complexes. X‐ray crystal structures of [Ca4(tmhd)4(OEt)4(EtOH)4], [Ca4(tmhd)6 (OCH2CH2NMe2)2], and [H2Ba4(tmhd)6(OCH2CH2OPri)4] . Inorg. Chem. , 34 : 5295 – 5306 .
   Google Scholar
• Kuzmina , N. , Ryazanov , M. and Troyanov , S. 1999 . Synthesis, crystal structure and thermal behaviour of Ba(hfa)2(Phen)2 and the crystal structure of Ba2(hfa)2(μ2‐CF3COO)2(Phen)4 (hfa=hexafluoroacetylacetonate, Phen=o‐Phenanthroline) . Polyhedron , 18 : 2177 – 2184 .
   Google Scholar
• Marchetti , F. , Pettinari , C. , Pettinari , R. , Cingolani , A. , Drozdov , A. and Troyanov , S. 2002 . A new family of ionic dinuclear strontium (imH2)2[Sr2(Q)6] compounds (imH=imidazole; QH=1‐phenyl‐3‐methyl‐ 4‐acylpyrazol‐5‐one) . J. Chem. Soc. Dalton Trans. , : 2616 – 2623 .
   Google Scholar
• Pettinari , C. , Marchetti , F. , Cingolani , A. , Leonesi , D. , Troyanov , S. and Drozdov , A. 1999 . New co‐ordination compounds derived from barium(II) and the anionic 4‐tert‐butylacetyl‐3‐methyl‐1‐phenylpyrazol‐5‐onate ligand (Q2). Crystal and molecular structure of [Ba2Q4(H2O)4], [Ba2Q4‐(Him)4], [BaQ2(tetraglyme)] (tetraglyme 5 2,5,8,11,14‐pentaoxapentadecane) and [BaQ2(phen)2] . J. Chem. Soc. Dalton Trans. , : 1555 – 1562 .
   Google Scholar
• Starosta , W. , Ptasiewicz‐bak , H. and Leciejewicz , J. 2004 . The crystal structure of a novel calcium(ii) complex with pyrazine‐2,6‐dicarboxylate . J. Coord. Chem. , 57 : 167 – 173 .
   Web of Science ®Google Scholar
• Ullström , A.‐S. , Warminska , D. and Persson , I. 2005 . The structure of dimethylsulfoxide‐solvated magnesium and calcium ions in solution and the solid state, and an overview of the coordination chemistry of hydrated and solvated alkaline earth metal ions . J. Coord. Chem. , 58 : 611 – 622 .
   Web of Science ®Google Scholar
• Zasurskaya , L. A. , Polyakova , I. N. , Polynova , T. N. , Poznyak , A. L. and Sergienko , V. S. 2002 . Crystal Structure of Calcium trans‐N‐(Nitrilotriacetato)(pyridine‐2‐arboxylato)cobaltate(III) Hexahydrate, Ca[Co(Nta)(Pic)]2 · 6H2O . Crystallogr. Rep. , 47 : 783 – 790 .
   Web of Science ®Google Scholar
• Yan , Z. , Day , C. S. and Lachga , A. 2005 . The first coordination polymers and hydrogen bonded networks containing octahedral Nb6 clusters and alkaline earth metal complexes . Inorg. Chem. , 44 : 4499 – 4505 .
   PubMed Web of Science ®Google Scholar
• Hundal , G. , Hundal , M. S. , Obrai , S. , Poonia , N. S. and Kumar , S. 2002 . Metal complexes of tetrapodal ligands: Synthesis, spectroscopic and thermal studies, and X‐ray crystal structure studies of Na(I), Ca(II), Sr(II), and Ba(II) complexes of tetrapodal ligands N,N,N′,N′‐Tetrakis(2‐hydroxypropyl)ethylenediamine and N,N,N,N′‐Tetrakis(2‐hydroxyethyl)ethylenediamine . Inorg. Chem. , 41 : 2077 – 2086 .
   PubMed Web of Science ®Google Scholar
• Sheldrick , G. M. 1997 . “ SHELXS‐97: Program for crystal structure solution ” . Germany : University of Göttingen .
   Google Scholar
• Sheldrick , G. M. 1997 . “ SHELXL‐97: Program for crystal structure refinement ” . Germany : University of Göttingen .
   Google Scholar