Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C—H...π and C—Br...π interactions

Girisha, Marisiddaiah; Sagar, Belakavadi K.; Yathirajan, H. S.; Rathore, R. S.; Glidewell, Christopher

doi:10.1107/s205322961700105x

Cited by 7 publications

(4 citation statements)

References 28 publications

(32 reference statements)

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“…There appears to be the formation of hydrogen bonding between the methylene group of epoxy coated oxidized PAN-CF with the ester group (C@O) and NAH group of nylon 6 matrix. The bond energies of NAH is 391 kJ/ mol, OAH is 467 kJ/mol, C@O is 799 kJ/mol, NAHAO is 8 kJ/ mol [39], and C@OAH group is 21 kJ/mol [40]. This indicates that the bond energy and bond dissociation energy of C@OAH is very much greater than NAHAO bond.…”

Section: Ftir Resultsmentioning

confidence: 99%

Microstructural characterization of short glass fiber and PAN based carbon fiber reinforced nylon 6 polymer composites

Munirajappa

Basavaraju

2017

Polymer Engineering & Sci

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Microstructural characterization of nylon 6/short glass fiber (SGF) and nylon 6/polyacrolonitrile based carbon fibers (PAN‐CFs) of 10 to 40 wt% has been performed by positron lifetime technique (PLT). The positron lifetime parameters viz., o‐Ps lifetime (τ3), o‐Ps intensity (I3), and fractional free volume (Fv) of nylon 6/SGF and nylon 6/PAN‐CF composites are correlated with the mechanical properties viz., tensile strength and Young's modulus. The Fv shows negative deviation with the reinforcement of 10 to 40 wt% of PAN‐CF and show positive deviation in nylon 6/SGF from the linear additivity relation. The negative deviation in nylon 6/PAN‐CF composite suggests the induced molecular packing due to the chemical interaction between the polymeric chains of nylon 6 and PAN‐CF. The positive deviation in nylon 6/SGF composite indicates the formation of interface between the polymeric chains of nylon 6 and SGF. The increased crystallinity of nylon 6/SGF and nylon 6/PAN‐CF composites shows the improved mechanical properties of the composites. The hydrodynamic interaction parameter (h), which shows more negative values in nylon 6/SGF than nylon 6/PAN‐CF composites. However, the extent of chemical interaction in nylon 6/SGF is less compare to nylon 6/PAN‐CF composites. This is evident from Fourier transform infrared spectrometry studies. POLYM. ENG. SCI., 58:1428–1437, 2018. © 2017 Society of Plastics Engineers

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Section: Ftir Resultsmentioning

confidence: 99%

Microstructural characterization of short glass fiber and PAN based carbon fiber reinforced nylon 6 polymer composites

Munirajappa

Basavaraju

2017

Polymer Engineering & Sci

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“…5a). In addition, a weak C-BrÁ Á Á v interaction [3.7100 (11) Å and 152.17 (9) ; symmetry code: (v) Àx + 1, y + 1 2 , Àz + 3 2 ] (Girisha et al, 2017) is present and stabilizes the crystal structure (Fig. 6a).…”

Section: Compoundmentioning

confidence: 99%

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

2018

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Nine salts of the antifolate drugs trimethoprim and pyrimethamine, namely, trimethoprimium [or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate monohydrate (TMPDCTPC, 1:1), CHNO·CHClOS, (I), trimethoprimium 3-bromothiophene-2-carboxylate monohydrate, (TMPBTPC, 1:1:1), CHNO·CHBrOS·HO, (II), trimethoprimium 3-chlorothiophene-2-carboxylate monohydrate (TMPCTPC, 1:1:1), CHNO·CHClOS·HO, (III), trimethoprimium 5-methylthiophene-2-carboxylate monohydrate (TMPMTPC, 1:1:1), CHNO·CHOS·HO, (IV), trimethoprimium anthracene-9-carboxylate sesquihydrate (TMPAC, 2:2:3), CHNO·CHO·1.5HO, (V), pyrimethaminium [or 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate (PMNDCTPC, 1:1), CHClN·CHClOS, (VI), pyrimethaminium 5-bromothiophene-2-carboxylate (PMNBTPC, 1:1), CHClN·CHBrOS, (VII), pyrimethaminium anthracene-9-carboxylate ethanol monosolvate monohydrate (PMNAC, 1:1:1:1), CHClN·CHO·CHOH·HO, (VIII), and bis(pyrimethaminium) naphthalene-1,5-disulfonate (PMNNSA, 2:1), 2CHClN·CHOS, (IX), have been prepared and characterized by single-crystal X-ray diffraction. In all the crystal structures, the pyrimidine N1 atom is protonated. In salts (I)-(III) and (VI)-(IX), the 2-aminopyrimidinium cation interacts with the corresponding anion via a pair of N-H...O hydrogen bonds, generating the robust R(8) supramolecular heterosynthon. In salt (IV), instead of forming the R(8) heterosynthon, the carboxylate group bridges two pyrimidinium cations via N-H...O hydrogen bonds. In salt (V), one of the carboxylate O atoms bridges the N1-H group and a 2-amino H atom of the pyrimidinium cation to form a smaller R(6) ring instead of the R(8) ring. In salt (IX), the sulfonate O atoms mimic the role of carboxylate O atoms in forming an R(8) ring motif. In salts (II)-(IX), the pyrimidinium cation forms base pairs via a pair of N-H...N hydrogen bonds, generating a ring motif [R(8) homosynthon]. Compounds (II) and (III) are isomorphous. The quadruple DDAA (D = hydrogen-bond donor and A = hydrogen-bond acceptor) array is observed in (I). In salts (II)-(IV) and (VI)-(IX), quadruple DADA arrays are present. In salts (VI) and (VII), both DADA and DDAA arrays co-exist. The crystal structures are further stabilized by π-π stacking interactions [in (I), (V) and (VII)-(IX)], C-H...π interactions [in (IV)-(V) and (VII)-(IX)], C-Br...π interactions [in (II)] and C-Cl...π interactions [in (I), (III) and (VI)]. Cl...O and Cl...Cl halogen-bond interactions are present in (I) and (VI), with distances and angles of 3.0020 (18) and 3.5159 (16) Å, and 165.56 (10) and 154.81 (11)°, respectively.

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“…Weak C-HÁ Á ÁF hydrogen bonds with similar bond lengths and bond angles to those in the title compound have been reported in the crystal structures of N-(3,5-difluorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide and N-(2,4,6-trifluorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide (Schwarzer & Weber, 2011), 2,3,5,6tetrafluorobenzene-1,4-diol quinoxaline (Czapik & Gdaniec, 2010) and 2,3-difluoro-N-(4-pyridyl)benzamide (McMahon et al, 2008). N-HÁ Á Á interactions are present in the structures discussed by Fun et al (2009) and Thirumurugan et al (1999) while C-HÁ Á Á interactions are present in the structures discussed by Selvanayagam et al (2015), Muralikrishna et al (2012) and Girisha et al (2017).…”

Section: Figurementioning

confidence: 91%

Crystal structure and Hirshfeld surface analysis of 2,4,6,11-tetrakis(4-fluorophenyl)-9-oxa-1,5-diazatricyclo[5.3.1.0^3.8]undecane

Vengatesh

Sundaravadivelu

2018

Acta Cryst E

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Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C—H...π and C—Br...π interactions

Abstract: Supporting information: this article has supporting information at journals.iucr.org/c Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C-HÁ Á Áp and C-BrÁ Á Áp interactions

Cited by 7 publications

References 28 publications

Microstructural characterization of short glass fiber and PAN based carbon fiber reinforced nylon 6 polymer composites

Microstructural characterization of short glass fiber and PAN based carbon fiber reinforced nylon 6 polymer composites

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Crystal structure and Hirshfeld surface analysis of 2,4,6,11-tetrakis(4-fluorophenyl)-9-oxa-1,5-diazatricyclo[5.3.1.0^3.8]undecane

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Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C—H...π and C—Br...π interactions

Abstract: Supporting information: this article has supporting information at journals.iucr.org/c Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C-HÁ Á Áp and C-BrÁ Á Áp interactions

Cited by 7 publications

References 28 publications

Microstructural characterization of short glass fiber and PAN based carbon fiber reinforced nylon 6 polymer composites

Microstructural characterization of short glass fiber and PAN based carbon fiber reinforced nylon 6 polymer composites

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Crystal structure and Hirshfeld surface analysis of 2,4,6,11-tetrakis(4-fluorophenyl)-9-oxa-1,5-diazatricyclo[5.3.1.03.8]undecane

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Crystal structure and Hirshfeld surface analysis of 2,4,6,11-tetrakis(4-fluorophenyl)-9-oxa-1,5-diazatricyclo[5.3.1.0^3.8]undecane