6-Benzyl-sulfanyl-9H-purine
Ismat Fatima1, Munawar Ali Munawar, Misbahul Ain Khan
1Institute of Chemistry, University of the Punjab, New Campus, Lahore, Pakistan.
Summary
This study details the crystal structure of a purine derivative, C(12)H(10)N(4)S. The phenyl ring is significantly rotated relative to the purine system, with hydrogen bonds stabilizing the overall crystal structure.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Purine derivatives are important in medicinal chemistry and materials science.
- Understanding the solid-state structure of organic compounds is crucial for predicting their properties.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(12)H(10)N(4)S.
- To analyze the spatial arrangement of the phenyl and purine rings.
- To identify intermolecular interactions stabilizing the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles.
- Identification of hydrogen bonding networks.
Main Results:
- The crystal structure of C(12)H(10)N(4)S was successfully determined.
- A significant dihedral angle of 76.65° was observed between the phenyl and purine rings.
- Intermolecular N-H⋯N hydrogen bonds were identified as key stabilizing interactions.
Conclusions:
- The determined crystal structure provides fundamental insights into the solid-state behavior of this purine derivative.
- The observed molecular conformation and hydrogen bonding pattern are critical for understanding crystal packing and potential intermolecular interactions.
- This structural information can guide the design of related compounds with tailored properties.
Related Concept Videos
01:22Electrophilic Aromatic Substitution: Sulfonation of Benzene
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
01:37NMR Spectroscopy of Benzene Derivatives
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
01:23Nomenclature of Aromatic Compounds with a Single Substituent
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
01:11Nomenclature of Aromatic Compounds with Multiple Substituents
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
01:13Five-Membered Heterocyclic Aromatic Compounds: Overview
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
01:25Basicity of Heterocyclic Aromatic Amines
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).