African Journal of Pure and Applied Chemistry
Subscribe to AJPAC
Full Name*
Email Address*

Article Number - A0B8D9C60136


Vol.10(4), pp. 42-55 , August 2016
DOI: 10.5897/AJPAC2016.0687
ISSN: 1996-0840



Full Length Research Paper

Preparation, structural and thermal studies of boroxine adducts having aryl boronic acids and pyrazoles



Hezil Hassan
  • Hezil Hassan
  • Department of Chemistry, Iran University of Science and Technology, Narmak, 16846-13114, Tehran, Iran.
  • Google Scholar







 Received: 02 April 2016  Accepted: 27 May 2016  Published: 31 August 2016

Copyright © 2016 Author(s) retain the copyright of this article.
This article is published under the terms of the Creative Commons Attribution License 4.0


Four new boroxine adducts ((B3O3(Ph)3PzH) (1), (B3O3(Ph)3(PztBu,iPrH)2) (2), (B3O3(PhF2)3PzH). PzH (3) and (B3O3(PhF2)3(PztBu,iPrH)2) (4)) using phenylboronic acid, 3,5-difluorophenylboronic acid, 1H-pyrazole (PzH) and 3-tert-butyl-5-isopropyl pyrazole (PztBu,iPrH) were prepared and characterized by elemental analysis, IR, 1H-NMR and X-ray diffraction. The crystallographic study reveals that PzH and PztBu,iPrH are bonded to boroxine molecule through B-N dative bond. It also demonstrates the different type of hydrogen bond interactions between adjacent molecules. The thermal stability of these adducts was investigated by TGA.

Key words: Boroxine, crystal structures, hydrogen bonding, thermal study.

Beckett MA, Strickland GC, Varma KS, Hibbs DE, Hursthouse MB, Abdul Malik KM (1995). Synthesis and characterization of amine adducts of tri(4-tolyl)boroxine and tri(3,5-xylyl)boroxine: molecular structure of (4-MeC6H4)3B3O3•cyclohexylamine. Polyhed.14:2623-2630.
Crossref

 

Bhat KL, Markham GD, Larkin JD, Bock CW (2011). Thermodynamics of Boroxine Formation from the Aliphatic Boronic Acid Monomers R–B(OH)2 (R = H, H3C, H2N, HO, and F): A Computational Investigation. J. Phys. Chem. A 115:7785-7793.
Crossref

 

Brandenburg K (2000). DIAMOND, Version 2.1c, Visual crystal structure information system, Crystal impact GbR, Bonn, Germany.

 

Cote AP, Benin AI, Ockwig NW, O'Keefe M, Matzger AJ, Yaghi OM (2005). Porous, crystalline, covalent organic frameworks. Science. 310:1166-1170.
Crossref

 

Davis AP, James TD (2005) in: Schrader, T, Hamilton, AD (ed) In functional synthetic receptors, Wiley-VCH, Weinheim.

 

Domingo SM, Jorge GA, Herbert H (2008). 3-Pyridineboronic acid → boroxine → pentadecanuclear boron cage → 3D molecular network: a sequence based on two levels of self-complementary self-assembly. Chem. Commun. 48:6543-6545.

 

Elfeky SA, Flower SE, Masumoto N, D'Hooge F, Labarthe L, Chen W, Len C, James TD, Fossey JS (2010). Diol appended quenchers for fluorescein boronic acid. Chem Asian J. 5:581-588.
Crossref

 

Faniran JA, Shurvell HF (1968). Infrared spectra of phenylboronic acid (normal and deuterated) and diphenyl phenylboronate. Can. J. Chem. 46:2089-2095.
Crossref

 

Fossey JS, James TD (2011). in: Gale, PA, Steed, JW (ed) In supramolecular chemistry, Wiley-VCH, Weinheim.

 

Fujita N, Shinkai S, James TD (2008). Boronic Acids in Molecular Self‐Assembly. Chem. Asian J. 3:1076-1091.
Crossref

 

Höpfi H (1999). The tetrahedral character of the boron atom newly defined—a useful tool to evaluate the N→B bond. J. Organomet. Chem. 581:129-149.
Crossref

 

Icli B, Sheepwash E, Riis-Johannessen T, Schenk K, Filinchuk Y, Scopelliti R, Severin K (2011). Dative boron–nitrogen bonds in structural supramolecular chemistry: multicomponent assembly of prismatic organic cages. Chem. Sci. 2:1719-1721.
Crossref

 

Imai S, Fujisawa K, Kobayashi T, Shirasawa N, Fujii H, Yoshimura T, Kitajima N, Moro-oka Y (1998). 63Cu NMR Study of Copper(I) Carbonyl Complexes with Various Hydrotris(pyrazolyl)borates:  Correlation between 63Cu Chemical Shifts and CO Stretching Vibrations. Inorg. Chem. 37:3066-3070.
Crossref

 

Iovine PM, Gyselbrecht CR, Perttu EK, Klick C, Neuwelt A, Loera J, DiPasquale AG, Rheingold AL, Kua J (2008). Hetero-arylboroxines: the first rational synthesis, X-ray crystallographic and computational analysis. Dalton Trans. 29:3791-3794.
Crossref

 

James TD (2005). in: Hall, DG (ed) In boronic acids in organic synthesis and chemical biology, Wiley-VCH, Weinheim.

 

Jorge CH, Domingo SM, Javier HP, Iran FHA, Herbert H (2012). N-containing boronic esters as self-complementary building blocks for the assembly of 2D and 3D molecular networks. Chem. Commun. 48:4241-4243.
Crossref

 

Jorge CH, Gonzalo CA, Höpfl H, Patricia RC, Viviana RM, Jorge GÁ, Domingo SM, Norberto FG (2016). Self-Assembly of Triphenylboroxine and the Phenylboronic Ester of Pentaerythritol with Piperazine, trans-1,4-Diaminocyclohexane, and 4-Aminopyridine. Eur. J. Inorg. Chem. 2016:355-365.
Crossref

 

Kua J, Iovine PM (2005). Formation of Para-Substituted Triphenylboroxines:  A Computational Study. J. Phys. Chem. A 109:8938-8943.
Crossref

 

Li X, Pennington J, Stobaugh JF, Schoneich C (2008). Synthesis of sulfonamide- and sulfonyl-phenylboronic acid-modified silica phases for boronate affinity chromatography at physiological pH. Anal Biochem. 372:227-336.
Crossref

 

Mehta MA, Fujinami T (1997). Li+ Transference number enhancement in polymer electrolytes by incorporation of anion trapping boroxine rings into the polymer host. Chem. Lett. 9:915-916.
Crossref

 

Melikova SM, Rutkowski KS, Rodziewicz P, Koll A (2002). FT-IR Studies of CH...B Interactions in Fluoroform Containing Cryosolutions. Polish J. Chem. 76:1271-1285.

 

MERCURY, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK. 

View

 

Miyaura N, Suzuki A (1995). Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 95:2457-2483.
Crossref

 

Morgan AB, Jurs JL, Tour JM (2000). Synthesis, flame-retardancy testing, and preliminary mechanism studies of nonhalogenated aromatic boronic acids: A new class of condensed-phase polymer flame-retardant additives for acrylonitrile–butadiene–styrene and polycarbonate. J. Appl. Polym. Sci. 76:1257-1268.
Crossref

 

Nishiyabu R, Kubo Y, James TD, Fossey JS (2011). Boronic acid building blocks: tools for self assembly. Chem Comm. 47(4):1124-1150.
Crossref

 

Phillips MD, James TD (2004). Boronic acid based modular fluorescent sensors for glucose. J. Fluoresc. 14:549-559.
Crossref

 

Saha S, Kottalanka RK, Panda TK, Harms K, Dehnen S, Nayek HP (2013). Syntheses, characterization and reactivity of Lewis acid–base adducts based on B–N dative bonds. J. Organomet. Chem. 745-746:329-334.
Crossref

 

Sarma R, Baruah B (2009). B•••π-aromatic and C–H•••B interactions in co-crystals of aromatic amine N-oxides with p-phenylenediboronic acid. J. Mol. Struct. 920: 350-354.
Crossref

 

Sheepwash E, Krampl V, Scopelliti R, Sereda O, Neels A, Severin K (2011). Molecular Networks Based on Dative Boron–Nitrogen Bonds. Angew. Chem. 50:3034-3037.
Crossref

 

Sheepwash E, Zhou K, Scopelliti R, Severin K (2013). Self-Assembly of Arylboronate Esters with Pyridyl Side Chains. Eur. J. Inorg. Chem. 14:2558-2563.
Crossref

 

Sheldrick GM (1990). Phase annealing in SHELX-90: direct methods for larger structures. Acta Cryst. A46:467-473.
Crossref

 

Sheldrick GM (1996). SADABS: Program for empirical absorption correction of area detector data. University of Gottingen: Gottingen, Germany.

 

Sheldrick GM (2000). SHELXTL-NT, Version 6.12, Reference manual, University of Gottingen, Germany.

 

Smith MK, Northrop BH (2014). Vibrational Properties of Boroxine Anhydride and Boronate Ester Materials: Model Systems for the Diagnostic Characterization of Covalent Organic Frameworks. Chem. Mater. 26:3781-3795.
Crossref

 

Snyder HR, Konecky MS, Lennarz WJ (1958). Aryl Boronic Acids. II. Aryl Boronic Anhydrides and their Amine Complexes. J. Am. Chem. Soc. 80:3611-3615.
Crossref

 

Striegler S (2003). Selective carbohydrate recognition by synthetic receptors in aqueous solution. Curr. Org. Chem. 7:81-102.
Crossref

 

Türker L, Gümüş S, Atalar T (2009). Structural and Molecular Orbital Properties of Some Boroxine Derivatives-A Theoretical Study. Bull Korean Chem. Soc. 30:2233-2239.
Crossref

 

Wimmer MA, Lochnit G, Bassil E, Muhling KH, Goldbach HE (2009). Membrane-Associated, Boron-Interacting Proteins Isolated by Boronate Affinity Chromatography. Plant Cell Physiol. 50:1292-1304.
Crossref

 

Wu QG, Wu G, Brancaleon L, Wang S (1999). B3O3Ph3(7-azaindole):  Structure, Luminescence, and Fluxionality. Organometal. 18(13):2553-2556.
Crossref

 

Yang Y, Inoue T, Fujinami T, Mehta MA (2002). Ionic conductivity and interfacial properties of polymer electrolytes based on PEO and boroxine ring polymer. J. Appl. Polym. Sci. 84:17-21.
Crossref

 


APA Hassan, H. (2016). Preparation, structural and thermal studies of boroxine adducts having aryl boronic acids and pyrazoles. African Journal of Pure and Applied Chemistry, 10(4), 42-55.
Chicago Hezil Hassan. "Preparation, structural and thermal studies of boroxine adducts having aryl boronic acids and pyrazoles." African Journal of Pure and Applied Chemistry 10, no. 4 (2016): 42-55.
MLA Hezil Hassan. "Preparation, structural and thermal studies of boroxine adducts having aryl boronic acids and pyrazoles." African Journal of Pure and Applied Chemistry 10.4 (2016): 42-55.
   
DOI 10.5897/AJPAC2016.0687
URL http://academicjournals.org/journal/AJPAC/article-abstract/A0B8D9C60136

Subscription Form