همنهشت، ساختار بلوری و آنالیز سطح هیرشفلد نمک اسیدی [4-متیل فنیل آمونیوم] [(O-فنیل)(هیدروکسیل)فسفات]، [4-CH3-C6H4NH3][(C6H5O)P(O)(O)(OH)]

نویسندگان

1 دانشگاه فردوسی مشهد

2 Masaryk University

چکیده

 همنهشت (سنتز) و آنالیز با پراش پرتو X نمک اسیدی [۴-متیل فنیل آمونیوم][(O-فنیل)(هیدروکسیل)فسفات]،
 [۴-CH۳-C۶H۴NH۳][(C۶H۵O)P(O)(O)(OH)]، گزارش شده­اند. این ترکیب در سیستم بلوری تک­میل، گروه فضایی P < /em>۲۱/c
(Å (۴)۵۱۴۷/۹a = ، Å (۱۰)۲۱۵۸/۲۳b = ، Å (۶)۲۷۴۰/۱۳c =  و °(۴)۲۴۴/۱۱۱β = ) و با چهار جزء مستقل شامل دو کاتیون و دو آنیون در واحد بی تقارن تبلور یافته است. در ساختار بلوری، اجزای مجاور به صورت پیوندهای هیدروژنی N–H…O و O–H…O به یکدیگر متصل شده، و آرایشی نردبانی موازی با محور [۱۰۰] را ایجاد کرده­اند. آنالیز سطح هیرشفلد و نمودار دو بعدی اثر انگشتی برای بررسی برهم­کنش­های موجود در ساختار مورد استفاده قرار گرفت. برهم­کنش­های N–H…O و O–H…O (نواحی سرخ در سطح هیرشفلد) برهم­کنش­های شاخص بوده و در نمودارهای رد ­انگشتی دو آنیون مستقل، دو شاخک شاخص به برهم­کنشO…H(O)  و نیز در نمودار مربوط به دو کاتیون مستقل، تک شاخک شاخص به برهم­کنشO…H(N)  تخصیص داده شد.     

کلیدواژه‌ها


عنوان مقاله [English]

Synthesis, crystal structure and Hirshfeld surface analysis of acidic salt [4-methyl phenyl ammonium][(O-phenyl)(hydroxyl)phosphate], [4-CH3-C6H4NH3][(C6H5O)P(O)(O)(OH)]

چکیده [English]

The synthesis and X-ray diffraction analysis of a new acidic salt, [4-methyl-phenyl ammonium][(O-phenyl)(hydroxyl)phosphate], [4-CH3-C6H4NH3][(C6H5O)P(O)(O)(OH)], is reported. This compound crystallizes in the monoclinic system, with space group P < /em>21/c
(a = 9.5147(4) Å, b = 23.2158(10) Å, c = 13.2740(6) Å and b = 111.244(4)°) with four independent components including two cations and two anions in the asymmetric unit. In the crystal, adjacent components are linked together through N–H∙∙∙O and O–H∙∙∙O hydrogen bonds building a ladder arrangement along [100] axis. The Hirshfeld surface analysis and two-dimensional fingerprint plot were used to study intermolecular interactions in the structure. The N–H∙∙∙O and O–H∙∙∙O hydrogen bonds are the characteristic interactions (red areas in the Hirshfeld surfaces). Two sharp spikes in the fingerprint plots of two anions are related to the O…H(O) contacts, while one nearly sharp spike in the fingerprint of two cations is assigned to the O...H(N) contacts.

کلیدواژه‌ها [English]

  • Acidic salt [4-methyl phenyl ammonium][(O-phenyl)(hydroxyl)phosphate]
  • X-ray diffraction analysis
  • hydrogen bonding
  • Hirshfeld surface analysis
[1] Ślepokura K., Lis T., "Structure of dihydroxyacetone phosphate dimethyl acetal, a stable dihydroxyacetone phosphate precursor, in the crystalline state", Carbohydrate Research 341 (2006) 507–524.

[2] Wisser B., Janiak C., "5,5'-Diamino-2,2'-bipyridin-1,1'-diium bis(5,5'-diamino-2,2'-bipyridin-1-ium) tetrakis(rac-1,1'-binaphthalene-2,2'-diylphosphate) hexahydrate: a two- dimensional supramolecular hydrogen-bonded network", Acta Crystallographica E63 (2007) o2871–o2872.

[3] Pourayoubi M., Sabbaghi F., "N-Benzyl-2-propanaminium O–methyltrichloroacetamidophosphate", Acta Crystallographica E63 (2007) p. o4366.

[4] Yazdanbakhsh M., Sabbaghi F., "N-Benzylpropan-2-aminium (benzylisopropylamido)(2,2,2-trifluoroacetamido)-phosphate", Acta Crystallographica E63 (2007) p. o4318.

[5] Gholivand K., Zare K., Afshar F., Shariatinia Z., Khavasi H. R., "4-Carbamoylpyridinium dihydrogen phosphate", Acta Crystallographica E63 (2007) p. 4027.

[6] Gholivand K., Pourayoubi M., Shariatinia Z., Molani S., "Crystal structure of tert-butylammonium trifluoroacetyl-N-(tert-butylamino) dioxophosphate acetonitrile solvate hydrate", Zeitschrift für Kristallographie-New Crystal Structures 220 (2005) 387–389.

[7] Gholivand K., Pourayoubi M., "Crystal structure of cyclohexyl-tert-butylammonium dichlorophosphate, (C10H20NH2)PCl2O2", Zeitschrift für Kristallographie-New Crystal Structures 219 (2004) 314–316.

[8] Hunter T., "Protein kinases and phosphatases", Cell 80 (1995) 225–236.

[9] Kumara Swamy C. K., Satish Kumar N., "New features in pentacoordinate phosphorus chemistry", Accounts of Chemical Research 39 (2006) 324–333.

[10] Mallender W., Szegletes T., Rosenberry T., "Acetylthiocholine binds to Asp74 at the peripheral site of human acetylcholinesterase as the first step in the catalytic pathway", Biochemistry 39 (2000) 7753–7763.

[11] Baldwin A., Huang Z., Jounaidi Y., Waxman D., "Identification of novel enzyme–prodrug combinations for use in cytochrome P450-based gene therapy for cancer", Archives of Biochemistry and Biophysics 409 (2003) 197–206.

[12] Pang Y., Kollmeyer T., Hong F., Lee J., Hammond P., Haugabouk S., Brimijoin S.,"Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators", Chemistry & Biology 10 (2003) 491–502.

[13] Zhou S., Lin K., Yang H., Li L., Liu W., Li J.,"Stereoisomeric separation and toxicity of a new organophosphorus insecticide chloramidophos", Chemical Research in Toxicology 20 (2007) 400–405.

[14] Nguyen C., Kim J., "Thermal stabilities and flame retardancies of nitrogen–phosphorus flame retardants based on bisphosphoramidates" Polymer Degradation and Stability 93 (2008) 1037–1043.

[15] Wolff S. K., Grimwood D. J., McKinnon J. J., Jayatilaka D., Spackman M. A., "Crystal Explorer 3.1" University of Western Australia, Perth, 2007.

[16] Madan Kumar S., Manjunath B. C., Lingaraju G. S., Abdoh M. M. M., Sadashiva M. P., Lokanath N. K., "A Hirshfeld surface analysis and crystal structure of 2'-[1-(2-fluoro-phenyl)-1H-tetrazol-5-Yl]-4-methoxy-biphenyl-2-carbaldehyde", Crystal structure theory and applications 2 (2013) 124–131.

[17] Pourayoubi M., Saneei A., Dušek M., Alemi Rostami S., Crochet A., Kučeraková M., "Two new organotin (IV)–phosphoryl complexes: crystal structure and Hirshfeld surface analysis", Journal of the Iranian Chemical Society 12 (2015) 2093–2103.

[18] Alamdar A. H., Pourayoubi M., Saneei A., Dušek M., Kučeraková M., Henriques M. S., "Hirshfeld surface analysis of two new phosphorothioic triamide structures", Acta Crystallographica C71 (2015) 824–833.

[19] Sheldrick G. M., "A short history of SHELX", Acta Crystallographica A64 (2008) 112–122.

[20] Pourayoubi M., Karimi Ahmadabad F., Eshtiagh-Hosseini H., Kučeráková M., Eigner V., Dušek M., "New rac-XP(O)(OC6H5)(NHC6H4-p-CH3) [X = N(CH3)(cyclo-C6H11) and NH(C3H5)] and rac-(C6H5CH2NH)P(O)(OC6H5)(NH-cyclo-C6H11) mixed-amide phosphinates", Acta Crystallographica C69 (2013) 1181–1185.

[21] Corbridge D. E. C. “Phosphorus, an outline of its chemistry, biochemistry and technology”, (1995) Elsevier: The Netherlands.

[22] Steiner T., "The hydrogen bond in the solid state", Angewandte chemie international edition. 41 (2002) 48–76.