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| 001 | 453844 | ||
| 005 | 20250729151217.0 | ||
| 024 | 7 | _ | |a 10.1039/C9CP06304H |2 doi |
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| 100 | 1 | _ | |a Brezesinski, G. |0 P:(DE-H253)PIP1008088 |b 0 |
| 245 | _ | _ | |a Lattice and thermodynamic characteristics of N -stearoyl-allo-threonine monolayers |
| 260 | _ | _ | |a Cambridge |c 2020 |b RSC Publ. |
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| 520 | _ | _ | |a The effect of the second chiral center of diastereomeric N-alkanoyl-allo-threonine on the main monolayer characteristics has been investigated. The characteristic features of the enantiomeric and racemic forms of N-stearoyl-allo-threonine monolayers are studied on a thermodynamic basis and molecular scale. The $π$–A curves of the enantiomeric and racemic allo-forms show similar features to those of N-stearoyl-threonine. The compression curves are always located above the corresponding decompression curves and the decompression curves can be used as equilibrium isotherms for both the enantiomeric and racemic N-stearoyl-allo-threonine. The absolute T$_0$-values (disappearance of the LE/LC-transition) are 4–5 K larger compared with the corresponding N-stearoyl-threonines, but the $Δ$T$_0$ between the enantiomeric (D) and the racemic (DL) forms is only slightly larger than that of N-stearoyl-threonine. The difference in the critical temperatures T$_c$, above which the monolayer cannot be compressed into the condensed state, between the enantiomeric and the racemic forms, is quite small ($Δ$T$_c$ = 0.8 K) and is smaller compared to that of the corresponding threonines ($Δ$T$_c$ = 1.8 K). This is consistent with the dominance of the van der Waals interactions between the alkyl chains reducing the influence of chirality on the thermodynamic parameters. GIXD studies of N-stearoyl-allo-threonine monolayers provide information about the lattice structure of condensed monolayer phases on the Angstrom scale and stipulate the homochiral or heterochiral preference in the condensed phases. Comparable to N-stearoyl-threonine, the enantiomers exhibit an oblique lattice structure, whereas the racemates form a NNN tilted orthorhombic structure demonstrating the dominance of heterochiral interactions in the racemates independent of the diasteomeric structure change of the polar head group. The A$_0$ values are characteristic for rotator phases. The smaller A$_0$ value obtained for the racemic monolayers indicates their tighter packing caused by heterochiral interactions. The program Hardpack was used to predict the geometric parameters of possible 2-dimensional packings. For comparison with the experimental GIXD data, the two-dimensional lattice parameters and characteristic features of the enantiomeric and racemic diastereomeric stearoyl-threonine monolayers were calculated and are in reasonable agreement with the experimental GIXD data. |
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| 700 | 1 | _ | |a Rudert, R. |0 P:(DE-HGF)0 |b 1 |
| 700 | 1 | _ | |a Vollhardt, D. |0 0000-0002-5297-4638 |b 2 |e Corresponding author |
| 773 | _ | _ | |a 10.1039/C9CP06304H |g Vol. 22, no. 5, p. 2783 - 2791 |0 PERI:(DE-600)1476244-4 |n 5 |p 2783 - 2791 |t Physical chemistry, chemical physics |v 22 |y 2020 |x 1463-9084 |
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