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In the absence of any leveling effect, the acid strength of binary compounds of hydrogen with nonmetals (A) increases as the H-A bond strength decreases down a group in the periodic table. For group 17, the order of increasing acidity is HF < HCl < HBr < HI. Likewise, for group 16, the order of increasing acid strength is H2O < H2S < H2Se < H2Te. Across a row in the periodic table, the acid strength of binary hydrogen compounds increases with...
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Carboxylic acids are the strongest among organic acids, as they readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion. In comparison, the acid derivatives lack acidic hydrogens directly attached to a functional group. In these compounds, the acidic nature arises from their ability to lose α hydrogens, making them weakly acidic.
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Carboxylic acids with lower molecular weight exhibit a sharp and unpleasant odor. They also have higher boiling and melting points than analogous compounds, such as aldehydes, ketones, and alcohols.
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Fulminic acid: a quasibent spectacle.

Ashley M Allen1, Laura N Olive1, Patricia A Gonzalez Franco1

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Physical Chemistry Chemical Physics : PCCP
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Summary
This summary is machine-generated.

Fulminic acid (HCNO) has a puzzlingly flat bending potential. Advanced electronic structure calculations reveal its equilibrium structure depends on the level of theory, with the most rigorous methods predicting a linear molecule.

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Area of Science:

  • Computational Chemistry
  • Theoretical Chemistry
  • Physical Chemistry

Background:

  • Fulminic acid (HCNO) has a complex and enigmatic H-C-N bending potential, posing challenges for electronic structure theory.
  • Over 200 years of research have sought to definitively determine the structure and properties of fulminic acid and its isomers.
  • Previous theoretical studies showed significant variations in predicted structures based on computational methods and basis sets.

Purpose of the Study:

  • To accurately determine the equilibrium geometry and vibrational frequencies of fulminic acid using rigorous ab initio wavefunction methods.
  • To resolve the long-standing debate regarding the linearity or bent nature of the fulminic acid molecule.
  • To calculate the reaction energy for HCN + O(3P) → HCNO.

Main Methods:

  • Employed focal point analyses (FPA) to extrapolate to the ab initio limit for geometries and frequencies.
  • Utilized extensive electron correlation treatments up to CCSDTQP(H) and complete basis set (CBS) extrapolations with cc-pCVXZ (X = 4-6) basis sets.
  • Included core electron correlation, scalar relativistic effects (MVD1), and diagonal Born-Oppenheimer corrections (DBOC).

Main Results:

  • At the AE-CCSD(T)/CBS level, HCNO was predicted to be linear with a bending frequency (ω5) of 120 cm-1.
  • Higher-level composite calculations (AE-CCSDT(Q)/CBS) yielded an imaginary frequency (51i cm-1) at linearity, indicating a bent equilibrium structure (173.9° H-C-N angle).
  • The most comprehensive calculations (AE-CCSDTQ(P)/CBS) including MVD1 and DBOC effects predicted a linear HCNO with ω5 = 32 cm-1.

Conclusions:

  • The equilibrium structure of fulminic acid is highly sensitive to the level of electron correlation and basis set used.
  • The most accurate theoretical predictions, including all relevant physical effects, suggest that vibrationless fulminic acid is linear.
  • The study provides a definitive benchmark for the properties of fulminic acid, resolving its 'quasibent' appellation.