Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.5K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.5K
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

5.7K
The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the...
5.7K
Carbocations02:10

Carbocations

11.4K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
11.4K
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

4.4K
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
4.4K
Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

2.7K
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
2.7K
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

3.4K
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
3.4K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Thiol-Retaining N-Terminal Cysteine Chemistry for Dual Modification and Bicyclic Peptide Construction.

Journal of the American Chemical Society·2026
Same author

A Single Bioorthogonal Reaction for Multiplex Cell Surface Protein Labeling.

Journal of the American Chemical Society·2025
Same author

Selective Protein Degradation through Tetrazine Ligation of Genetically Incorporated Unnatural Amino Acids.

Chemistry, an Asian journal·2024
Same author

Secondary Amine Catalysis in Enzyme Design: Broadening Protein Template Diversity through Genetic Code Expansion.

Angewandte Chemie (International ed. in English)·2024
Same author

Multiple C-H⋯anion and N-H⋯anion hydrogen bond directed two-dimensional crystalline nanosheets with precise distance control of surface charges for enhanced DNA capture.

Soft matter·2021
Same author

Organic room-temperature phosphorescence from halogen-bonded organic frameworks: hidden electronic effects in rigidified chromophores.

Chemical science·2021

Related Experiment Video

Updated: Aug 16, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

9.1K

Why does thionating a carbonyl molecule make it a better electron acceptor?

Yi-Lin Wu1, Anna I Wright1

  • 1School of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK. wuyl@cardiff.ac.uk.

Physical Chemistry Chemical Physics : PCCP
|December 20, 2022
PubMed
Summary

Thiocarbonyl molecules show promise in biomedical and materials science due to their unique electronic properties. Natural bond orbital analysis explains their enhanced electron affinity, aiding in the design of new materials.

More Related Videos

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

9.3K
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

8.1K

Related Experiment Videos

Last Updated: Aug 16, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

9.1K
Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

9.3K
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

8.1K

Area of Science:

  • Materials Science
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Thiocarbonyl molecules (R₂C=S) have gained traction in biomedical and materials applications.
  • Their utility stems from a small visible optical gap and enhanced electron affinity compared to carbonyls (R₂C=O).

Purpose of the Study:

  • To explain the electronic properties of thiocarbonyls and their analogues.
  • To provide a predictive rule for designing novel π-conjugated materials incorporating heavy heteroelements.

Main Methods:

  • Natural Bond Orbital (NBO) analysis was employed to investigate electronic structures.
  • Computational analysis focused on the Lowest Unoccupied Molecular Orbital (LUMO) lowering effect.

Main Results:

  • NBO analysis revealed that weaker C=S antibonding interactions, due to sulfur's 3p orbital, lower the LUMO.
  • This contrasts with stronger C=O antibonding interactions involving oxygen's 2p orbital.
  • The study provides insights into the electronic effects of substituents on (thio)carbonyl functionalities.

Conclusions:

  • The electronic properties of thiocarbonyls are explained by orbital interactions, not just electronegativity.
  • A predictive framework is established for tuning electronic properties of π-conjugated systems with heavy heteroelements.
  • This facilitates the development of advanced materials for various applications.