Synthesis and Complexation Studies of Heterocyclic Compounds With Two or Three Contiguous Hydrogen Bonding Sites

Murray, Thomas James

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Description

Title

Synthesis and Complexation Studies of Heterocyclic Compounds With Two or Three Contiguous Hydrogen Bonding Sites

Author(s)

Murray, Thomas James

Issue Date

1994

Doctoral Committee Chair(s)

Zimmerman, Steven C.

Department of Study

Chemistry

Discipline

Chemistry

Degree Granting Institution

University of Illinois at Urbana-Champaign

Degree Name

Ph.D.

Degree Level

Dissertation

Keyword(s)

Chemistry, Organic

Abstract

• The design and synthesis of heterocyclic compounds with two or three adjacent hydrogen bonding sites is described. A general synthetic methodology was developed to produce 5-substituted anthyridine analogs. These compounds exhibited increased stability over the unsubstituted anthyridines. A novel hydrogen bond donor-donor-acceptor (DDA) unit was synthesized to mimic the hydrogen bond functionality of guanosine. A guanosine receptor was developed to ascertain the negative steric interactions inherent in Hamilton's guanosine receptor.
• New doubly and triply hydrogen bonded complexes with every possible arrangement of hydrogen bond donor (D) and acceptor (A) groups (AD-DA, AA-DD, ADA-DAD, AAD-DDA, AAA-DDD) were studied. The self-association of guanosine was investigated and the resultant dimer was found to favor the Watson-Crick arrangement over the Hoogsteen. Free energies of complexation of doubly hydrogen bonded complexes ranged from 0.4 to 4.7 kcal mol$\sp{-1}$ while the triply hydrogen bonded complex association energies ranged from 2.4 to 7.0 kcal mol$\sp{-1}$. The effect of hydrogen bond donors and acceptors that do not participate in primary hydrogen bonds was also examined.

Graduation Semester

1994

Type of Resource

text

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