Related Experiment Video
Updated: Sep 19, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
From Norbornadiene to Norcamphor and Camphor: Reduced-Cost Semiexperimental Structural Refinement from Limited
Lina Uribe1,2, Marco Mendolicchio1, Sofia Municio3
1Scuola Normale Superiore di Pisa, Piazza dei Cavalieri 7, 56126 Pisa, Italy.
Abstract:
We present an efficient semiexperimental protocol for determining spectroscopically accurate molecular structures from limited isotopologue data with a focus on medium-sized organic molecules. The availability of all monosubstituted isotopologues of norbornadiene enabled the determination of a complete semiexperimental (reqSE) equilibrium structure, establishing a reference for validating reduced-dimensionality approaches that avoid deuterium substitution. The rotational spectrum of norcamphor is reported here for the first time, providing a critical benchmark for assessing the method's accuracy. By combining composite quantum-chemical calculations with a cost-effective vibrational correction scheme, the protocol achieves near-spectroscopic accuracy while substantially reducing the computational effort. This approach enables the structural characterization of large systems where extensive isotopic substitution is impractical, thereby broadening the applicability of semiexperimental methods in modern molecular spectroscopy.
Related Concept Videos
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Alcohols from Carbonyl Compounds: Reduction
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

