Structure of propionamide at 123 K

Usanmaz, Ali; Adler, G.

doi:10.1107/s0567740882003707

Cited by 15 publications

(18 citation statements)

References 4 publications

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“…36 The crystal unit cell is monoclinic ( P 2 1 / c space group), with four molecules per unit cell (Figure S1). The measured crystallographic axes and angles are a = 8.851(4) Å, b = 5.750(2) Å, c = 9.766(3) Å, and β = 114.780(15)°.…”

Section: Resultsmentioning

confidence: 99%

UV Resonance Raman Investigation of the Aqueous Solvation Dependence of Primary Amide Vibrations

et al. 2015

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We investigated the normal mode composition and the aqueous solvation dependence of the primary amide vibrations of propanamide. Infrared, normal Raman, and UV resonance Raman (UVRR) spectroscopy were applied in conjunction with density functional theory (DFT) to assign the vibrations of crystalline propanamide. We examined the aqueous solvation dependence of the primary amide UVRR bands by measuring spectra in different acetonitrile/water mixtures. As previously observed in the UVRR spectra of N-methylacetamide, all of the resonance enhanced primary amide bands, except for the Amide I (AmI), show increased UVRR cross sections as the solvent becomes water-rich. These spectral trends are rationalized by a model wherein the hydrogen bonding and the high dielectric constant of water stabilizes the ground state dipolar − O -C=NH 2 + resonance structure over the neutral O=C-NH 2 resonance structure. Thus, vibrations with large C-N stretching show increased UVRR cross sections because the C-N displacement between the electronic ground and excited state increases along the C-N bond. In contrast, vibrations dominated by C=O stretching, such as the AmI, show a decreased displacement between the electronic ground and excited state, which result in a decreased UVRR cross section upon aqueous solvation. The UVRR primary amide vibrations can be used as sensitive spectroscopic markers to study the local dielectric constant and hydrogen bonding environments of the primary amide side chains of glutamine (Gln) and asparagine (Asn). Graphical Abstract *Corresponding Author: asher@pitt.edu. NotesThe authors declare no competing financial interest. Tables S1-S6 and Figures S1-S3. Description of X-ray crystallographic methods to determine structure of propanamide and UVRR spectral deconvolution methods. This material is available free of charge via the Internet at http://pubs.acs.org/. Supporting Information

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Section: Resultsmentioning

confidence: 99%

UV Resonance Raman Investigation of the Aqueous Solvation Dependence of Primary Amide Vibrations

et al. 2015

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“…Two subsets of structures can be defined for comparison: ambient-and high-pressure polymorphs. The ambient-pressure polymorphs of formamide and acetamide are not isostructural with those of propionamide and other higher amides [1]. When comparing dimer-forming structures only ( Figure 5), that is excluding acetamide-I, graph-set analysis indicates the presence of a basic 5 6 ( 20) R motif; upon closer inspection, the spatial arrangement of this motif is clearly different in the three compounds ( Figure 5): in formamide-II and propionamide-II, this motif is similar and propagates to form H-bonded sheets.…”

Section: Structural Comparison With Other Amidesmentioning

confidence: 94%

“…Crystallisation by slow evaporation from an acetone/benzene mixture had been reported previously [1]. Crystals of form I were grown by slow evaporation of either an aqueous solution of propionamide (Sigma-Aldrich, Germany) at 278 K or a 1:1 (vol/vol) acetone/o-xylene solution at 293 K.…”

Section: Methodsmentioning

confidence: 99%

“…Propionamide, CH 3 CH 2 CONH 2 , is the third member of the homologous series of aliphatic amides of the types RCONH 2 and the second member that is a solid at ambient temperature (melting point: 353.7 K) [1]. The unit-cell parameters and space group (P2 1 /a) of the ambienttemperature crystal structure, form I herein, were first reported in 1955 by Turner and Lingafelter [2], CSD [3] reference code ZZZKAY.…”

Section: Introductionmentioning

confidence: 97%

“…The unit-cell parameters and space group (P2 1 /a) of the ambienttemperature crystal structure, form I herein, were first reported in 1955 by Turner and Lingafelter [2], CSD [3] reference code ZZZKAY. In 1982, the 123 K structure in the standard P2 1 /c space group was published, CSD reference code ZZZKAY01 [1]. The basic supramolecular synthon in the crystal structure of propionamide is the centrosymmetric H-bonded dimer, a common and robust synthon for all aliphatic amides.…”

Section: Introductionmentioning

confidence: 99%

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A high-pressure polymorph of propionamide from in situ high-pressure crystallisation from solution

Fabbiani

Pulham²,

Warren

2014

Zeitschrift Für Kristallographie - Crystalline Materials

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The structure of a high-pressure polymorph of propionamide is reported from synchrotron single-crystal X-ray diffraction data. The polymorph was obtained by in situ high-pressure crystallisation from solution in a diamond-anvil cell at 0.9 GPa; its structure is 23% denser than that of the ambient-pressure polymorph at STP. PIXEL lattice and dimer energies calculations indicate that the ambientand high-pressure polymorphs are energetically competitive. Together with acetamide and formamide, this is the third high-pressure polymorph of an aliphatic amide crystallising as a Z′ = 2 structure; the H-bonded network is however significantly different from the ones reported for the other two compounds. This study highlights the power of in situ high-pressure crystallisation techniques for accessing novel polymorphic forms of molecular compounds.

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Acyl‐ und Alkylidenarsane. VI. Vergleichende Untersuchungen zur Struktur von Bis (2,2‐dimethylpropionyl) phenylarsan und ‐phosphan

Becker

Birkhahn³

et al. 1985

Zeitschrift anorg allge chemie

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Die aus den entsprechenden Bis(trimethylsilyl)‐Derivaten und 2,2‐Dimethylpropionylchlorid zugänglichen Verbindungen Bis(2,2‐dimethylpropionyl)phenylarsan 1a [19] und ‐phosphan 1b [20] kristallisieren monoklin in der Raumgruppe P21/c mit den bei einer Meßtemperatur von −70 ± 3°C/ −73 ± 3°C bestimmten Abmessungen der Elementarzelle: a = 1449,3(7)/1468,3(3); b = 1050,0(5)/985,9(2); c = 1138,5(4)/1159,4(4) pm; β = 108,27(3)/105;61(3)°; Z = 4. Nach den Ergebnissen von Röntgenstrukturanalysen (Rw = 0,044/0,044) weisen sowohl das Arsan 1a als auch das Phosphan 1b Abstände zwischen Pnikogen‐ und Carbonylkohlen‐stoffatom auf, die mit Mittelwerten von 205 und 191 pm wie in den Trifluormethyl‐Verbindungen [2] gegenüber dem Standard (194 bzw. 183 pm) eindeutig verlängert sind. Weitere charakteristische mittlere Bindungslängen und ‐winkel sind: AsC(Phenyl) 194; PC(Phenyl) 184; CO 119/121; C(O)C 153/154 pm; C(O)AsC(O) 91; C(O)PC(O) 95; AsCO 120; AsC(O)C 117 und PC(O)C 118°.

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Structure of propionamide at 123 K

Cited by 15 publications

References 4 publications

UV Resonance Raman Investigation of the Aqueous Solvation Dependence of Primary Amide Vibrations

UV Resonance Raman Investigation of the Aqueous Solvation Dependence of Primary Amide Vibrations

A high-pressure polymorph of propionamide from in situ high-pressure crystallisation from solution

Acyl‐ und Alkylidenarsane. VI. Vergleichende Untersuchungen zur Struktur von Bis (2,2‐dimethylpropionyl) phenylarsan und ‐phosphan

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