5-<i>O</i>-Acetyl-<scp>D</scp>-ribono-1,4-lactone

Bortoluzzi, Adaı́lton J.; Sebrão, Damianni; Sá, Marcus M.; Nascimento, Maria G.

doi:10.1107/s1600536811038670

Cited by 5 publications

(2 citation statements)

References 13 publications

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“…Therefore, the synthesis of new carbohydrate-based molecules often relies on single crystal X-ray analysis for correct structural and conformational assignments (Booth et al, 2009;Czugler & Pinté r, 2011;Sales & Silveira, 2015). In a continuation of our research on the chemistry of carbohydrates (Bortoluzzi et al, 2011;Cardoso et al, 2015;Sá et al, 2002Sá et al, , 2008Sebrã o et al, 2011), we describe herein the crystal structure of 5-O-benzoyl-2,3-Oisopropylidene-d-ribono-1,4-lactone, C 15 H 16 O 6 , (I).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 5-O-benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

2017

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In the title compound, obtained from the acylation reaction between 2,3-O-isopropylidene-d-ribono-1,4-lactone and benzoyl chloride, the known absolute configuration for the lactone moiety of the ester substituent has been confirmed. The five-membered rings of the bicyclic lactone–dioxolane moiety both show envelope conformations and form a dihedral angle of 19.82 (7)° between the lactone ring and the benzene ring.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 5-O-benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

2017

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“…A dashed green line connects C2 and C2b. Color code: red O, gray C, green centroids.Example 3: Two-fold screw rotation40 In this example (Figure5), it is again possible to identify unique pairs of putatively symmetryrelated atoms. Starting from the terminal methyl, the chain can be followed pairing C1/C1b, C2/C2b, O1/O1b, O2/O2b, and C3/C3b.…”

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confidence: 99%

Computer-Aided Identification of Symmetry Relating Groups of Molecules

Ruiz

Johnstone

2020

J. Chem. Educ.

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Molecular symmetry plays an important role in many areas of chemistry, and students are generally taught to identify intramolecular symmetries at the undergraduate level. Intermolecular symmetry, the symmetry among groups of molecules, is of great importance in topics such as X-ray crystallography, but it receives substantially less attention. Even when familiar with such symmetries as translations, screw rotations, and glide reflections, students rarely obtain the same level of proficiency in identifying these symmetries via inspection as they do with the proper and improper rotations involved in pointgroup symmetry. We describe a tool designed to scaffold the student's ability to mentally manipulate molecules and identify the presence and nature of intermolecular symmetry. The tool consists of an algorithm that the student follows to generate centroids between atoms in putatively symmetry-related molecules. The easily recognized patterns formed by the centroids provide key information about the presence and nature of any intermolecular symmetry relating the molecules. The theoretical basis for the patterns formed by the centroids is provided along with worked examples, an example problem set, and a prescription for generating new exercises.

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Alkoxycarbonyl Groups in Metalloesters Showing Oxocarbenium‐like Structure and Alkylating Reactivity

Xu,

Feng,

et al. 2024

Angewandte Chemie

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In contrast to the well‐documented acylating reactivity, the alkylating reactivity of the alkoxycarbonyl group, as signified by its oxocarbenium‐like resonance structure, remains almost unexplored. Herein, the first series of Co/Ni dinuclear metalloesters exhibiting the novel oxocarbenium‐like alkoxycarbonyl groups were synthesized and characterized. In these deformed alkoxycarbonyl groups, the Ccarbonyl–Oalkoxyl bonds were contracted to 1.177(11) ~ 1.191(9) Å with the elongations of the Ccarbonyl=Ocarbonyl bonds to 1.368(13) ~ 1.441(9) Å. Meanwhile, the O–Calkyl bonds were also elongated to 1.522(11) ~ 1.607(15) Å, and were by far the longest O–Calkyl bonds reported for alkoxycarbonyl groups. As triggered by the long O‐Calkyl distances, the alkylating reactivity of the oxocarbenium‐like methoxycarbonyl group towards a series of C/N/O‐nucleophiles via the rare BAL2 mechanism at ambient conditions was examined. Furthermore, the homo‐etherifications of alcohols mediated by the Co/Ni dinuclear metalloesters were investigated. The yields followed the trend ethanol >> n‐propanol >> n‐butanol ≈ n‐pentanol, that closely related to the structure features of the alkoxycarbonyl groups in corresponding metalloesters: while the ethoxycarbonyl group showed the reactive oxocarbenium‐like framework, the n‐propoxycarbonyl group displayed the dioxocarbenium‐like skeleton with a shorter O–Calkyl bond; In comparison, the classical frameworks with unactivated alkyl moieties were observed for n‐butoxycarbonyl and n‐pentoxycarbonyl groups.

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5-O-Acetyl-D-ribono-1,4-lactone

Cited by 5 publications

References 13 publications

Crystal structure of 5-O-benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

Crystal structure of 5-O-benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

Computer-Aided Identification of Symmetry Relating Groups of Molecules

Alkoxycarbonyl Groups in Metalloesters Showing Oxocarbenium‐like Structure and Alkylating Reactivity

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