Structure of 3,6-dimethyl-1,4-dioxane-2,5-dione [<scp>D</scp>-,<scp>D</scp>-(<scp>L</scp>-,<scp>L</scp>-)lactide]

Hummel, G.J. van; Harkema, Sybolt; Kohn, F.E.; Feijén, Jan

doi:10.1107/s0567740882006840

Cited by 36 publications

(25 citation statements)

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“…For (L)‐ and (DL)‐lactide the NAHNOZ ( Z ′=3, Z = 12, P212121) and BICVIS (Z′=1, Z = 4 P21/c) structures were retrieved, respectively. For the pure enantiomer of 3‐chloromandelic acid, ( S )‐3ClMA, the TUYBIA (Z′=2, Z = 4, P21) and for the racemic molecular compound ( R , S )‐3ClMA the FIZPEL03 ( Z ′=1, Z = 4, P21/c) crystal structures were used.…”

Section: Methodsmentioning

confidence: 99%

Accurate lattice energies of organic molecular crystals from periodic turbomole calculations

Buchholz

Stein

2018

J Comput Chem

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Accurate lattice energies of organic crystals are important i.e. for the pharmaceutical industry. Periodic DFT calculations with atom-centered Gaussian basis functions with the Turbomole program are used to calculate lattice energies for several non-covalently bound organic molecular crystals. The accuracy and convergence of results with basis set size and k-space sampling from periodic calculations is evaluated for the two reference molecules benzoic acid and naphthalene. For the X23 benchmark set of small molecular crystals accurate lattice energies are obtained using the PBE-D3 functional. In particular for hydrogen-bonded systems, a sufficiently large basis set is required. The calculated lattice energy differences between enantiopure and racemic crystal forms for a prototype set of chiral molecules are in good agreement with experimental results and allow the rationalization and computer-aided design of chiral separation processes. © 2018 Wiley Periodicals, Inc.

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Section: Methodsmentioning

confidence: 99%

Accurate lattice energies of organic molecular crystals from periodic turbomole calculations

Buchholz

Stein

2018

J Comput Chem

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“…In the crystal cell of 1 (Fig. 2), all the 1,4-dioxane-2,5-dione rings are located in parallel planes at a distance of approximately 2.0 Å , but do not tend to form molecular stacks and organize the rings neither into columns, as reported for hemilactides bearing relatively small substituents, such as 3,6dimethyl-1,4-dioxane-2,5-dione (van Hummel et al, 1982) and 3-bromo-3,6-dimethyl-1,4-dioxane-2,5-dione and 3-methylene-6-methyl-1,4-dioxane-2,5-dione (Fiore et al, 2010), nor into supramolecular formations where one half of the parallel plane is perpendicular to the other, as reported in the cases of 3-benzyloxymethyl-6-methyl-1,4-dioxane-2,5-dione (Kooijman et al, 2005) and 3,6-diphenyl-l,4-dioxane-2,5-dione (Lynch et al, 1990). In addition, the crystal packing shows some short C-HÁ Á ÁO contacts (Table 1) leading to the pairwise molecular binding, i.e.…”

Section: Supramolecular Featuresmentioning

confidence: 69%

Synthesis and characterization of 3-methyl-6-[(propynyloxy)methyl]-1,4-dioxane-2,5-dione

2017

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The number of known asymmetrically substituted hemilactides, important precursors for obtaining regular derivatives of polylactide polymers, is still limited and structural characterization of most of them is incomplete. In the title racemic 1,4-dioxane-2,5-dione derivative, C 9 H 10 O 5 , the hemilactide heterocycle exhibits a twist-boat conformation. The bulkier propynyloxymethyl group is in an axial position with a gauche conformation for the CH 2 -O-CH 2 -C segment. In the crystal, molecules are linked by pairs of C-HÁ Á ÁO hydrogen bonds, forming inversion dimers. The dimers are linked by further C-HÁ Á ÁO contacts, forming a three-dimensional structure.

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“…These interactions were not reported for the previously studied morpholine-2,5-diones, which comprise mono-or disubstituted glycolidyl units. However, weak CÐHÁ Á ÁO intermolecular hydrogen bonds playing a decisive role in the crystal organization were also found in the related glycolide ring (Belen'kaya et al, 1997) and indeed in the lactide ring (van Hummel et al, 1982;Belen'kaya et al, 1997), the HÁ Á ÁO distances being within the 2.33±2.44 A Ê range.…”

Section: Figurementioning

confidence: 97%

Morpholine-2,5-dione

et al. 2006

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In the title compound, C4H5NO3, the morpholine ring adopts a boat conformation that is distorted towards twist-boat, the boat ends being the two Csp3 atoms of the ring. The molecular packing is stabilized by the establishment of strong intermolecular NH...OC hydrogen bonds, which give rise to centrosymmetric dimers, and a network of weak CH2...OC hydrogen bonds, where each dimer interacts with eight neighbouring morpholinedione rings.

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Structure of 3,6-dimethyl-1,4-dioxane-2,5-dione [D-,D-(L-,L-)lactide]

Cited by 36 publications

References 7 publications

Accurate lattice energies of organic molecular crystals from periodic turbomole calculations

Accurate lattice energies of organic molecular crystals from periodic turbomole calculations

Synthesis and characterization of 3-methyl-6-[(propynyloxy)methyl]-1,4-dioxane-2,5-dione

Morpholine-2,5-dione

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