7782-39-0

Usage

Chemical Description

Deuterium is a stable isotope of hydrogen used in labeling experiments to track the reaction path.

Uses

Used in Chemical Reaction Studies:
Deuterium is used as a tracer in the establishment of rates and kinetics of chemical reactions. Its distinct isotopic properties allow researchers to track and analyze reaction mechanisms and pathways more accurately.
Used in Thermonuclear Reactions:
Deuterium plays a crucial role in thermonuclear reactions, where it can be used to generate energy through nuclear fusion. This process involves the combination of deuterium and tritium isotopes, releasing a significant amount of energy.
Used in Cyclotrons:
Deuterium serves as a projectile in cyclotrons for bombardment of atomic nuclei. This process is utilized to synthesize isotopes of several transuranium elements, contributing to the field of nuclear research and development.
Used in Nuclear Reactors:
Deuterium oxide, D2O, or heavy water, is used as a neutron moderator in nuclear reactors. Its ability to slow down neutrons enhances the efficiency of nuclear fission reactions, making it an essential component in the operation of certain types of reactors.

History

Rutherford predicted the existence of this heavy isotope of hydrogen in 1920. It was detected by Urey, Brickwedde and Murphy in 1932. It occurs in all natural compounds of hydrogen including water, as well as in free hydrogen molecules at the ratio of about one part per 6,000 parts hydrogen.

Preparation

Deuterium may be prepared by several methods. Urey’s first method of preparation involved fractional distillation of a very large amount of liquid hydrogen. It also may be produced by electrolysis of heavy water obtained by H2S/H2O exchange process. It may be obtained by continued, long-time electrolysis of ordinary water in which light water molecules are split first, thus concentrating deuterated oxygen in the residual liquid. Also, deuterium in high purity may be separated by thermally induced diffusion processes.

Air & Water Reactions

Highly flammable.

Reactivity Profile

DEUTERIUM, like hydrogen, is a reducing agent; reacts readily with oxidizing agents.

Purification Methods

Pass the gas over activated charcoal at -195o [MacIver & Tobin J Phys Chem 64 451 1960]. Purify it also by diffusion through nickel [Pratt & Rogers, J Chem Soc, Faraday Trans I 92 1589 1976]. Always check deuterium for radioactivity to determine the amount of tritium in it (see D2O below).

InChI:InChI=1/H2/h1H/i1+1D

Synthetic route

benzoyl chloride (98-88-4) + p-nitrophenyl glycinate-2,2-d2 → p-nitrophenyl N-benzoylglycinate-2,2-d2 (7782-39-0)

Conditions	Yield
With TEA In hexane; ethyl acetate for 2h;	70%

4-nitro-phenol (100-02-7) + KOH-solution → p-nitrophenyl N-benzoylglycinate-2,2-d2 (7782-39-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: dicyclohexylcarboimide / CHCl3 / 3 h / 10 °C 2: 4 M HCl / dioxane / 0.25 h 3: 70 percent / TEA / ethyl acetate; hexane / 2 h View Scheme

p-nitrophenyl N-(tert-butoxycarbonyl)glycinate-2,2-d2 → p-nitrophenyl N-benzoylglycinate-2,2-d2 (7782-39-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4 M HCl / dioxane / 0.25 h 2: 70 percent / TEA / ethyl acetate; hexane / 2 h View Scheme

p-nitrophenyl N-benzoylglycinate-2,2-d2 (7782-39-0) → C9H5(2)H2NO2

Conditions	Yield
In water Rate constant; phosphate buffer;

Upstream product

• 98-88-4 benzoyl chloride 
• 100-02-7 4-nitro-phenol 

Relevant academic research and scientific papers

Rate-Controlling Step of Oxazolinone Formation. Secondary and Solvent Kinetic Isotope Effects

The β-deuterium secondary kinetic isotope effect for the formation of 2-phenyloxazolin-5-one in the alkaline hydrolysis of p-nitrophenyl n-benzoylglycinate (p-NO2C6H4O2CCL2NHOCC6H5, L = H or D) was determined to be kH/kD = 1.03 +/- 0.0.2 at temperatures between 10.5 and 40.0 deg C; activation parameters for the protium ester are ΔH(excit.) = 21.7 +/- 0.4 kcal mol-1 and ΔS(excit.)298 = 31.9 +/- 0.6 cal deg-1mol-1.These results, combined with those of previous studies, suggest that leaving-group expulsion is the only step contributing to rate limitation for conversion of the glycinate to the oxazolinone.The small, normal sec ondary isotope effect probably has complex origins, which may include relief of steric strain upon cyclization and hyperconjugative stabilization of the rate-controlling transition state.Apparent second-order rate constants for the formation of 2-phenyloxazolin-5-one in the alkaline hydrolysis of the isotopically unsubstituted ester were also obtained in aqueous solvent containing various mole fraction n of D2O (kn).The kinetic solvent effects (KSIE's) are inverse at all values of n with k1.0/k0 = 1.75.Analysis of the bowl-shaped plot of k1.0/k0 vs. n indicates that fractionation of the reactant lyoxide ion in the mixed isotopic waters predominates the KSIE.A small, normal transition-state effect of about 1.3 makes the KSIE less inverse than would be expected if the entire effect originated in lyoxide fractionation.