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Updated: May 15, 2026

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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
N,N-Dibenzyl-O,O'-dimethyl thio-phosphate
Akbar Raissi Shabari1, Fahimeh Sabbaghi, Mehrdad Pourayoubi
1Faculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran.
Acta Crystallographica. Section E, Structure Reports Online
|January 4, 2013
Summary
This study details the molecular structure of a novel organophosphorus compound, C(16)H(20)NO(2)PS. Analysis reveals a distorted tetrahedral environment around the phosphorus atom, indicating unique chemical bonding characteristics.
Area of Science:
- Organophosphorus Chemistry
- Crystallography
- Molecular Structure Analysis
Background:
- Organophosphorus compounds exhibit diverse chemical properties and applications.
- Understanding the precise molecular geometry is crucial for predicting reactivity and function.
Purpose of the Study:
- To elucidate the detailed molecular structure of the title compound, C(16)H(20)NO(2)PS.
- To characterize the bonding environment around the phosphorus and nitrogen atoms.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Analysis of bond lengths, bond angles, and atomic environments.
Main Results:
- The phosphorus atom is situated in a distorted tetrahedral P(S)(O)(2)N coordination geometry.
- Bond angles at the phosphorus atom range from 99.37(7)° to 115.68(5)°.
- The amido nitrogen atom exhibits sp(2) hybridization, confirmed by a bond-angle sum of 357.8°.
Conclusions:
- The determined structure provides fundamental insights into the stereochemistry of this organophosphorus compound.
- The sp(2) character of the nitrogen atom influences the overall molecular conformation and electronic distribution.
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Phosphodiester Linkages
Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
DNA and RNA are polynucleotides or long chains of nucleotides that are linked together. A nucleotide is...
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
DNA and RNA are polynucleotides or long chains of nucleotides that are linked together. A nucleotide is...
Preparation and Reactions of Thiols
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.
Preparation and Reactions of Sulfides
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

