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Related Concept Videos

Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Isomerism in Alkenes02:01

Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is bonded to two hydrogen atoms...
Nomenclature of Alkenes02:29

Nomenclature of Alkenes

The IUPAC naming system for alkenes replaces -an- with -en- in the corresponding parent alkanes. Accordingly, a simple alkene replaces the -ane suffix of the alkane with -ene.
As per the IUPAC rules, the longest carbon chain containing the maximum number of double bonds is identified as the parent chain and is numbered such that the doubly bonded carbon atoms receive the lowest possible numbers. The location of the double bond is indicated by the number of its first carbon atom. In branched...
Constitutional Isomers of Alkanes02:18

Constitutional Isomers of Alkanes

Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the branched isomers are given...

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The Brosimum allene: a structural revision.

Gaojie Hu1, Kai Liu, Lawrence J Williams

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.

Organic Letters
|November 14, 2008
PubMed
Summary
This summary is machine-generated.

Structural elucidation of mururin C, a natural product from Brosimum acutifolium, was revised using synthetic modeling and NMR data. The allenic structure A was corrected to the nonallenic structure B.

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Area of Science:

  • Natural Product Chemistry
  • Organic Synthesis
  • Spectroscopy

Background:

  • Brosimum acutifolium is a plant source of bioactive compounds.
  • Previous structural assignment of mururin C as an allenic compound (A) requires re-evaluation.

Purpose of the Study:

  • To revise the proposed allenic structure of mururin C.
  • To confirm the correct nonallenic structure (B) of this natural product.

Main Methods:

  • Computational modeling and synthesis of a proposed allenic structure.
  • Analysis of calculated carbon-13 Nuclear Magnetic Resonance ((13)C NMR) data.
  • Comparison of synthetic and calculated data with experimental findings.

Main Results:

  • Calculated (13)C NMR data from the synthetic allenic model did not match experimental data.
  • The nonallenic structure B, now identified as mururin C, aligns with experimental observations.

Conclusions:

  • The originally proposed allenic structure A for mururin C is incorrect.
  • Mururin C is confirmed as a nonallenic natural product with structure B.